| date | time | Home | score | Away | HT | |
| Round 1. | ||||||
| Sat 15.08.98 | 14:00 | Blackburn Rovers | 0-0 | Derby County | 0-0 | |
| Sat 15.08.98 | 14:00 | Coventry City | 2-1 | Chelsea | 2-1 | |
| Sat 15.08.98 | 14:00 | Everton | 0-0 | Aston Villa | 0-0 | |
| Sat 15.08.98 | 14:00 | Manchester United | 2-2 | Leicester City | 0-1 | |
| Sat 15.08.98 | 14:00 | Middlesbrough | 0-0 | Leeds United | 0-0 | |
| Sat 15.08.98 | 14:00 | Newcastle United | 0-0 | Charlton Athletic | 0-0 | |
| Sat 15.08.98 | 14:00 | Sheffield Wednesday | 0-1 | West Ham United | 0-0 | |
| Sat 15.08.98 | 14:00 | Wimbledon | 3-1 | Tottenham Hotspur | 0-0 | |
| Sun 16.08.98 | 15:00 | Southampton | 1-2 | Liverpool | 1-1 | |
| Mon 17.08.98 | 19:00 | Arsenal | 2-1 | Nottingham Forest | 0-0 | |
| Round 2. | ||||||
| Sat 22.08.98 | 14:00 | Charlton Athletic | 5-0 | Southampton | 1-0 | |
| Sat 22.08.98 | 14:00 | Chelsea | 1-1 | Newcastle United | 1-1 | |
| Sat 22.08.98 | 14:00 | Derby County | 0-0 | Wimbledon | 0-0 | |
| Sat 22.08.98 | 14:00 | Leicester City | 2-0 | Everton | 2-0 | |
| Sat 22.08.98 | 14:00 | Liverpool | 0-0 | Arsenal | 0-0 | |
| Sat 22.08.98 | 14:00 | Nottingham Forest | 1-0 | Coventry City | 0-0 | |
| Sat 22.08.98 | 14:00 | Tottenham Hotspur | 0-3 | Sheffield Wednesday | 0-2 | |
| Sat 22.08.98 | 14:00 | West Ham United | 0-0 | Manchester United | 0-0 | |
| Sun 23.08.98 | 15:00 | Aston Villa | 3-1 | Middlesbrough | 1-0 | |
| Mon 24.08.98 | 19:00 | Leeds United | 1-0 | Blackburn Rovers | 1-0 | |
| Round 3. | ||||||
| Sat 29.08.98 | 14:00 | Arsenal | 0-0 | Charlton Athletic | 0-0 | |
| Sat 29.08.98 | 14:00 | Blackburn Rovers | 1-0 | Leicester City | 1-0 | |
| Sat 29.08.98 | 14:00 | Coventry City | 0-0 | West Ham United | 0-0 | |
| Sat 29.08.98 | 14:00 | Everton | 0-1 | Tottenham Hotspur | 0-1 | |
| Sat 29.08.98 | 14:00 | Southampton | 1-2 | Nottingham Forest | 0-0 | |
| Sat 29.08.98 | 14:00 | Wimbledon | 1-1 | Leeds United | 0-0 | |
| Sat 29.08.98 | 14:00 | Middlesbrough | 1-1 | Derby County | 0-1 | |
| Sat 29.08.98 | 14:00 | Sheffield Wednesday | 0-1 | Aston Villa | 0-1 | |
| Sun 30.08.98 | 15:00 | Newcastle United | 1-4 | Liverpool | 1-4 | |
| Wed 16.12.98 | 18:45 | Manchester United | 1-1 | Chelsea | 1-0 | |
| Round 4. | ||||||
| Tue 08.09.98 | 19:00 | Manchester United | 4-1 | Charlton Athletic | 2-1 | |
| Tue 08.09.98 | 19:00 | Nottingham Forest | 0-2 | Everton | 0-0 | |
| Tue 08.09.98 | 19:00 | Leeds United | 3-0 | Southampton | 1-0 | |
| Wed 09.09.98 | 18:45 | Tottenham Hotspur | 2-1 | Blackburn Rovers | 1-1 | |
| Wed 09.09.98 | 18:45 | West Ham United | 3-4 | Wimbledon | 3-1 | |
| Wed 09.09.98 | 19:00 | Chelsea | 0-0 | Arsenal | 0-0 | |
| Wed 09.09.98 | 19:00 | Aston Villa | 1-0 | Newcastle United | 0-0 | |
| Wed 09.09.98 | 19:00 | Derby County | 1-0 | Sheffield Wednesday | 1-0 | |
| Wed 09.09.98 | 19:00 | Leicester City | 0-1 | Middlesbrough | 0-1 | |
| Wed 09.09.98 | 19:00 | Liverpool | 2-0 | Coventry City | 1-0 | |
| Round 5. | ||||||
| Sat 12.09.98 | 14:00 | Aston Villa | 2-0 | Wimbledon | 1-0 | |
| Sat 12.09.98 | 14:00 | Charlton Athletic | 1-2 | Derby County | 0-1 | |
| Sat 12.09.98 | 14:00 | Chelsea | 2-1 | Nottingham Forest | 2-0 | |
| Sat 12.09.98 | 14:00 | Everton | 0-0 | Leeds United | 0-0 | |
| Sat 12.09.98 | 14:00 | Leicester City | 1-1 | Arsenal | 1-0 | |
| Sat 12.09.98 | 14:00 | Manchester United | 2-0 | Coventry City | 1-0 | |
| Sat 12.09.98 | 14:00 | Newcastle United | 4-0 | Southampton | 2-0 | |
| Sat 12.09.98 | 14:00 | Sheffield Wednesday | 3-0 | Blackburn Rovers | 2-0 | |
| Sat 12.09.98 | 14:00 | West Ham United | 2-1 | Liverpool | 1-0 | |
| Sun 13.09.98 | 15:00 | Tottenham Hotspur | 0-3 | Middlesbrough | 0-2 | |
| Round 6. | ||||||
| Sat 19.09.98 | 14:00 | Coventry City | 1-5 | Newcastle United | 1-3 | |
| Sat 19.09.98 | 14:00 | Derby County | 2-0 | Leicester City | 1-0 | |
| Sat 19.09.98 | 14:00 | Leeds United | 0-0 | Aston Villa | 0-0 | |
| Sat 19.09.98 | 14:00 | Liverpool | 3-3 | Charlton Athletic | 1-1 | |
| Sat 19.09.98 | 14:00 | Middlesbrough | 2-2 | Everton | 2-0 | |
| Sat 19.09.98 | 14:00 | Nottingham Forest | 0-0 | West Ham United | 0-0 | |
| Sat 19.09.98 | 14:00 | Southampton | 1-1 | Tottenham Hotspur | 0-1 | |
| Sat 19.09.98 | 14:00 | Wimbledon | 2-1 | Sheffield Wednesday | 1-0 | |
| Sun 20.09.98 | 15:00 | Arsenal | 3-0 | Manchester United | 2-0 | |
| Mon 21.09.98 | 19:00 | Blackburn Rovers | 3-4 | Chelsea | 1-1 | |
| Round 7. | ||||||
| Thu 24.09.98 | 18:45 | Manchester United | 2-0 | Liverpool | 1-0 | |
| Sat 26.09.98 | 14:00 | Newcastle United | 2-0 | Nottingham Forest | 1-0 | |
| Sat 26.09.98 | 14:00 | Sheffield Wednesday | 1-0 | Arsenal | 0-0 | |
| Sat 26.09.98 | 14:00 | Tottenham Hotspur | 3-3 | Leeds United | 1-2 | |
| Sat 26.09.98 | 14:00 | Aston Villa | 1-0 | Derby County | 1-0 | |
| Sat 26.09.98 | 14:00 | Charlton Athletic | 1-1 | Coventry City | 0-0 | |
| Sat 26.09.98 | 14:00 | Chelsea | 2-0 | Middlesbrough | 0-0 | |
| Sat 26.09.98 | 14:00 | Everton | 0-0 | Blackburn Rovers | 0-0 | |
| Sun 27.09.98 | 15:00 | Leicester City | 1-1 | Wimbledon | 0-0 | |
| Mon 28.09.98 | 19:00 | West Ham United | 1-0 | Southampton | 0-0 | |
| Round 8. | ||||||
| Sat 03.10.98 | 14:00 | Blackburn Rovers | 3-0 | West Ham United | 1-0 | |
| Sat 03.10.98 | 14:00 | Coventry City | 1-2 | Aston Villa | 0-2 | |
| Sat 03.10.98 | 14:00 | Derby County | 0-1 | Tottenham Hotspur | 0-0 | |
| Sat 03.10.98 | 14:00 | Leeds United | 0-1 | Leicester City | 0-0 | |
| Sat 03.10.98 | 14:00 | Middlesbrough | 4-0 | Sheffield Wednesday | 2-0 | |
| Sat 03.10.98 | 14:00 | Nottingham Forest | 0-1 | Charlton Athletic | 0-1 | |
| Sat 03.10.98 | 14:00 | Southampton | 0-3 | Manchester United | 0-1 | |
| Sat 03.10.98 | 14:00 | Wimbledon | 1-2 | Everton | 1-1 | |
| Sun 04.10.98 | 14:00 | Liverpool | 1-1 | Chelsea | 0-1 | |
| Sun 04.10.98 | 15:00 | Arsenal | 3-0 | Newcastle United | 2-0 | |
| Round 9. | ||||||
| Sat 17.10.98 | 14:00 | Arsenal | 1-1 | Southampton | 1-0 | |
| Sat 17.10.98 | 14:00 | Chelsea | 2-1 | Charlton Athletic | 1-0 | |
| Sat 17.10.98 | 14:00 | Everton | 0-0 | Liverpool | 0-0 | |
| Sat 17.10.98 | 14:00 | Manchester United | 5-1 | Wimbledon | 2-1 | |
| Sat 17.10.98 | 14:00 | Middlesbrough | 2-1 | Blackburn Rovers | 0-0 | |
| Sat 17.10.98 | 14:00 | Newcastle United | 2-1 | Derby County | 2-0 | |
| Sat 17.10.98 | 14:00 | Nottingham Forest | 1-1 | Leeds United | 0-0 | |
| Sat 17.10.98 | 14:00 | West Ham United | 0-0 | Aston Villa | 0-0 | |
| Sun 18.10.98 | 15:00 | Coventry City | 1-0 | Sheffield Wednesday | 0-0 | |
| Mon 19.10.98 | 19:00 | Leicester City | 2-1 | Tottenham Hotspur | 1-1 | |
| Round 10. | ||||||
| Sat 24.10.98 | 14:00 | Aston Villa | 1-1 | Leicester City | 0-1 | |
| Sat 24.10.98 | 14:00 | Charlton Athletic | 4-2 | West Ham United | 1-2 | |
| Sat 24.10.98 | 14:00 | Derby County | 1-1 | Manchester United | 0-0 | |
| Sat 24.10.98 | 14:00 | Liverpool | 5-1 | Nottingham Forest | 3-1 | |
| Sat 24.10.98 | 14:00 | Sheffield Wednesday | 0-0 | Everton | 0-0 | |
| Sat 24.10.98 | 14:00 | Southampton | 2-1 | Coventry City | 2-0 | |
| Sat 24.10.98 | 14:00 | Tottenham Hotspur | 2-0 | Newcastle United | 1-0 | |
| Sat 24.10.98 | 14:00 | Wimbledon | 2-2 | Middlesbrough | 1-2 | |
| Sun 25.10.98 | 15:00 | Blackburn Rovers | 1-2 | Arsenal | 0-2 | |
| Sun 25.10.98 | 15:00 | Leeds United | 0-0 | Chelsea | 0-0 | |
| Round 11. | ||||||
| Sat 31.10.98 | 14:00 | Coventry City | 0-1 | Arsenal | 0-0 | |
| Sat 31.10.98 | 14:00 | Derby County | 2-2 | Leeds United | 1-2 | |
| Sat 31.10.98 | 14:00 | Everton | 1-4 | Manchester United | 1-2 | |
| Sat 31.10.98 | 14:00 | Leicester City | 1-0 | Liverpool | 0-0 | |
| Sat 31.10.98 | 14:00 | Newcastle United | 0-3 | West Ham United | 0-0 | |
| Sat 31.10.98 | 14:00 | Sheffield Wednesday | 0-0 | Southampton | 0-0 | |
| Sat 31.10.98 | 14:00 | Wimbledon | 1-1 | Blackburn Rovers | 0-0 | |
| Sun 01.11.98 | 15:00 | Middlesbrough | 1-1 | Nottingham Forest | 1-0 | |
| Mon 02.11.98 | 19:00 | Tottenham Hotspur | 2-2 | Charlton Athletic | 0-1 | |
| Wed 09.12.98 | 18:45 | Chelsea | 2-1 | Aston Villa | 1-1 | |
| Round 12. | ||||||
| Sat 07.11.98 | 10:30 | Southampton | 3-3 | Middlesbrough | 0-0 | |
| Sat 07.11.98 | 14:00 | Aston Villa | 3-2 | Tottenham Hotspur | 2-0 | |
| Sat 07.11.98 | 14:00 | Blackburn Rovers | 1-2 | Coventry City | 0-0 | |
| Sat 07.11.98 | 14:00 | Charlton Athletic | 0-0 | Leicester City | 0-0 | |
| Sat 07.11.98 | 14:00 | Liverpool | 1-2 | Derby County | 0-2 | |
| Sat 07.11.98 | 14:00 | Nottingham Forest | 0-1 | Wimbledon | 0-1 | |
| Sun 08.11.98 | 13:00 | Manchester United | 0-0 | Newcastle United | 0-0 | |
| Sun 08.11.98 | 13:00 | West Ham United | 1-1 | Chelsea | 1-0 | |
| Sun 08.11.98 | 14:00 | Leeds United | 2-1 | Sheffield Wednesday | 1-1 | |
| Sun 08.11.98 | 15:00 | Arsenal | 1-0 | Everton | 1-0 | |
| Round 13. | ||||||
| Sat 14.11.98 | 14:00 | Arsenal | 0-0 | Tottenham Hotspur | 0-0 | |
| Sat 14.11.98 | 14:00 | Charlton Athletic | 1-1 | Middlesbrough | 1-0 | |
| Sat 14.11.98 | 14:00 | Chelsea | 3-0 | Wimbledon | 1-0 | |
| Sat 14.11.98 | 14:00 | Liverpool | 1-3 | Leeds United | 0-0 | |
| Sat 14.11.98 | 14:00 | Manchester United | 3-2 | Blackburn Rovers | 2-0 | |
| Sat 14.11.98 | 14:00 | Newcastle United | 1-1 | Sheffield Wednesday | 1-0 | |
| Sat 14.11.98 | 14:00 | Southampton | 1-4 | Aston Villa | 0-1 | |
| Sat 14.11.98 | 14:00 | West Ham United | 3-2 | Leicester City | 1-1 | |
| Sun 15.11.98 | 15:00 | Coventry City | 3-0 | Everton | 1-0 | |
| Mon 16.11.98 | 19:00 | Nottingham Forest | 2-2 | Derby County | 0-0 | |
| Round 14. | ||||||
| Sat 21.11.98 | 14:00 | Aston Villa | 2-4 | Liverpool | 0-2 | |
| Sat 21.11.98 | 14:00 | Blackburn Rovers | 0-2 | Southampton | 0-1 | |
| Sat 21.11.98 | 14:00 | Leeds United | 4-1 | Charlton Athletic | 1-0 | |
| Sat 21.11.98 | 14:00 | Leicester City | 2-4 | Chelsea | 1-2 | |
| Sat 21.11.98 | 14:00 | Middlesbrough | 2-0 | Coventry City | 0-0 | |
| Sat 21.11.98 | 14:00 | Sheffield Wednesday | 3-1 | Manchester United | 1-1 | |
| Sat 21.11.98 | 14:00 | Tottenham Hotspur | 2-0 | Nottingham Forest | 0-0 | |
| Sat 21.11.98 | 14:00 | Wimbledon | 1-0 | Arsenal | 0-0 | |
| Sun 22.11.98 | 15:00 | Derby County | 0-2 | West Ham United | 0-1 | |
| Mon 23.11.98 | 19:00 | Everton | 1-0 | Newcastle United | 1-0 | |
| Round 15. | ||||||
| Sat 28.11.98 | 14:00 | Charlton Athletic | 1-2 | Everton | 0-1 | |
| Sat 28.11.98 | 14:00 | Chelsea | 1-1 | Sheffield Wednesday | 1-0 | |
| Sat 28.11.98 | 14:00 | Coventry City | 1-1 | Leicester City | 0-0 | |
| Sat 28.11.98 | 14:00 | Newcastle United | 3-1 | Wimbledon | 1-1 | |
| Sat 28.11.98 | 14:00 | Nottingham Forest | 2-2 | Aston Villa | 2-0 | |
| Sat 28.11.98 | 14:00 | Southampton | 0-1 | Derby County | 0-1 | |
| Sat 28.11.98 | 14:00 | West Ham United | 2-1 | Tottenham Hotspur | 1-0 | |
| Sun 29.11.98 | 14:00 | Liverpool | 2-0 | Blackburn Rovers | 2-0 | |
| Sun 29.11.98 | 14:00 | Manchester United | 3-2 | Leeds United | 1-1 | |
| Sun 29.11.98 | 15:00 | Arsenal | 1-1 | Middlesbrough | 0-1 | |
| Round 16. | ||||||
| Sat 05.12.98 | 14:00 | Aston Villa | 1-1 | Manchester United | 0-0 | |
| Sat 05.12.98 | 14:00 | Blackburn Rovers | 1-0 | Charlton Athletic | 0-0 | |
| Sat 05.12.98 | 14:00 | Derby County | 0-0 | Arsenal | 0-0 | |
| Sat 05.12.98 | 14:00 | Everton | 0-0 | Chelsea | 0-0 | |
| Sat 05.12.98 | 14:00 | Leeds United | 4-0 | West Ham United | 1-0 | |
| Sat 05.12.98 | 14:00 | Leicester City | 2-0 | Southampton | 1-0 | |
| Sat 05.12.98 | 14:00 | Tottenham Hotspur | 2-1 | Liverpool | 1-0 | |
| Sat 05.12.98 | 14:00 | Wimbledon | 2-1 | Coventry City | 0-0 | |
| Sun 06.12.98 | 15:00 | Middlesbrough | 2-2 | Newcastle United | 1-1 | |
| Mon 07.12.98 | 19:00 | Sheffield Wednesday | 3-2 | Nottingham Forest | 1-0 | |
| Round 17. | ||||||
| Sat 12.12.98 | 14:00 | Blackburn Rovers | 0-0 | Newcastle United | 0-0 | |
| Sat 12.12.98 | 14:00 | Derby County | 2-2 | Chelsea | 1-0 | |
| Sat 12.12.98 | 14:00 | Everton | 1-0 | Southampton | 1-0 | |
| Sat 12.12.98 | 14:00 | Leicester City | 3-1 | Nottingham Forest | 1-1 | |
| Sat 12.12.98 | 14:00 | Middlesbrough | 1-0 | West Ham United | 1-0 | |
| Sat 12.12.98 | 14:00 | Sheffield Wednesday | 3-0 | Charlton Athletic | 1-0 | |
| Sat 12.12.98 | 14:00 | Tottenham Hotspur | 2-2 | Manchester United | 0-2 | |
| Sun 13.12.98 | 14:00 | Wimbledon | 1-0 | Liverpool | 0-0 | |
| Sun 13.12.98 | 15:00 | Aston Villa | 3-2 | Arsenal | 0-2 | |
| Mon 14.12.98 | 19:00 | Leeds United | 2-0 | Coventry City | 1-0 | |
| Round 18. | ||||||
| Sat 19.12.98 | 14:00 | Chelsea | 2-0 | Tottenham Hotspur | 0-0 | |
| Sat 19.12.98 | 14:00 | Coventry City | 1-1 | Derby County | 1-0 | |
| Sat 19.12.98 | 14:00 | Liverpool | 2-0 | Sheffield Wednesday | 2-0 | |
| Sat 19.12.98 | 14:00 | Manchester United | 2-3 | Middlesbrough | 0-2 | |
| Sat 19.12.98 | 14:00 | Newcastle United | 1-0 | Leicester City | 0-0 | |
| Sat 19.12.98 | 14:00 | Nottingham Forest | 2-2 | Blackburn Rovers | 2-0 | |
| Sat 19.12.98 | 14:00 | Southampton | 3-1 | Wimbledon | 1-0 | |
| Sat 19.12.98 | 14:00 | West Ham United | 2-1 | Everton | 1-0 | |
| Sun 20.12.98 | 15:00 | Arsenal | 3-1 | Leeds United | 1-0 | |
| Mon 21.12.98 | 19:00 | Charlton Athletic | 0-1 | Aston Villa | 0-1 | |
| Round 19. | ||||||
| Sat 26.12.98 | 14:00 | Arsenal | 1-0 | West Ham United | 1-0 | |
| Sat 26.12.98 | 14:00 | Blackburn Rovers | 2-1 | Aston Villa | 1-0 | |
| Sat 26.12.98 | 14:00 | Coventry City | 1-1 | Tottenham Hotspur | 0-1 | |
| Sat 26.12.98 | 14:00 | Everton | 0-0 | Derby County | 0-0 | |
| Sat 26.12.98 | 14:00 | Manchester United | 3-0 | Nottingham Forest | 1-0 | |
| Sat 26.12.98 | 14:00 | Middlesbrough | 1-3 | Liverpool | 1-2 | |
| Sat 26.12.98 | 14:00 | Newcastle United | 0-3 | Leeds United | 0-1 | |
| Sat 26.12.98 | 14:00 | Sheffield Wednesday | 0-1 | Leicester City | 0-1 | |
| Sat 26.12.98 | 14:00 | Southampton | 0-2 | Chelsea | 0-1 | |
| Sat 26.12.98 | 14:00 | Wimbledon | 2-1 | Charlton Athletic | 1-1 | |
| Round 20. | ||||||
| Mon 28.12.98 | 15:00 | Aston Villa | 2-1 | Sheffield Wednesday | 1-1 | |
| Mon 28.12.98 | 15:00 | Charlton Athletic | 0-1 | Arsenal | 0-0 | |
| Mon 28.12.98 | 15:00 | Leicester City | 1-1 | Blackburn Rovers | 1-1 | |
| Mon 28.12.98 | 15:00 | West Ham United | 2-0 | Coventry City | 1-0 | |
| Mon 28.12.98 | 15:00 | Tottenham Hotspur | 4-1 | Everton | 1-1 | |
| Mon 28.12.98 | 15:00 | Nottingham Forest | 1-1 | Southampton | 0-0 | |
| Mon 28.12.98 | 15:00 | Liverpool | 4-2 | Newcastle United | 0-1 | |
| Mon 28.12.98 | 15:00 | Derby County | 2-1 | Middlesbrough | 1-0 | |
| Tue 29.12.98 | 18:45 | Chelsea | 0-0 | Manchester United | 0-0 | |
| Tue 29.12.98 | 18:45 | Leeds United | 2-2 | Wimbledon | 1-1 | |
| Round 21. | ||||||
| Sat 09.01.99 | 14:00 | Wimbledon | 2-1 | Derby County | 1-0 | |
| Sat 09.01.99 | 14:00 | Southampton | 3-1 | Charlton Athletic | 1-1 | |
| Sat 09.01.99 | 14:00 | Sheffield Wednesday | 0-0 | Tottenham Hotspur | 0-0 | |
| Sat 09.01.99 | 14:00 | Newcastle United | 0-1 | Chelsea | 0-1 | |
| Sat 09.01.99 | 14:00 | Middlesbrough | 0-0 | Aston Villa | 0-0 | |
| Sat 09.01.99 | 14:00 | Everton | 0-0 | Leicester City | 0-0 | |
| Sat 09.01.99 | 14:00 | Coventry City | 4-0 | Nottingham Forest | 1-0 | |
| Sat 09.01.99 | 14:00 | Blackburn Rovers | 1-0 | Leeds United | 1-0 | |
| Sat 09.01.99 | 14:00 | Arsenal | 0-0 | Liverpool | 0-0 | |
| Sun 10.01.99 | 15:00 | Manchester United | 4-1 | West Ham United | 2-0 | |
| Round 22. | ||||||
| Sat 16.01.99 | 14:00 | Liverpool | 7-1 | Southampton | 3-0 | |
| Sat 16.01.99 | 14:00 | Tottenham Hotspur | 0-0 | Wimbledon | 0-0 | |
| Sat 16.01.99 | 14:00 | West Ham United | 0-4 | Sheffield Wednesday | 0-2 | |
| Sat 16.01.99 | 14:00 | Nottingham Forest | 0-1 | Arsenal | 0-1 | |
| Sat 16.01.99 | 14:00 | Leicester City | 2-6 | Manchester United | 1-1 | |
| Sat 16.01.99 | 14:00 | Chelsea | 2-1 | Coventry City | 1-1 | |
| Sat 16.01.99 | 14:00 | Derby County | 1-0 | Blackburn Rovers | 0-0 | |
| Sat 16.01.99 | 14:00 | Leeds United | 2-0 | Middlesbrough | 2-0 | |
| Sun 17.01.99 | 15:00 | Charlton Athletic | 2-2 | Newcastle United | 0-1 | |
| Mon 18.01.99 | 19:00 | Aston Villa | 3-0 | Everton | 1-0 | |
| Round 23. | ||||||
| Sat 30.01.99 | 14:00 | Newcastle United | 2-1 | Aston Villa | 2-0 | |
| Sat 30.01.99 | 14:00 | Wimbledon | 0-0 | West Ham United | 0-0 | |
| Sat 30.01.99 | 14:00 | Middlesbrough | 0-0 | Leicester City | 0-0 | |
| Sat 30.01.99 | 14:00 | Everton | 0-1 | Nottingham Forest | 0-0 | |
| Sat 30.01.99 | 14:00 | Coventry City | 2-1 | Liverpool | 0-0 | |
| Sat 30.01.99 | 14:00 | Blackburn Rovers | 1-1 | Tottenham Hotspur | 1-0 | |
| Sat 30.01.99 | 14:00 | Southampton | 3-0 | Leeds United | 1-0 | |
| Sat 30.01.99 | 14:00 | Sheffield Wednesday | 0-1 | Derby County | 0-0 | |
| Sun 31.01.99 | 15:00 | Arsenal | 1-0 | Chelsea | 1-0 | |
| Sun 31.01.99 | 15:00 | Charlton Athletic | 0-1 | Manchester United | 0-0 | |
| Round 24. | ||||||
| Sat 06.02.99 | 14:00 | Chelsea | 1-0 | Southampton | 1-0 | |
| Sat 06.02.99 | 14:00 | Aston Villa | 1-3 | Blackburn Rovers | 0-1 | |
| Sat 06.02.99 | 14:00 | Leeds United | 0-1 | Newcastle United | 0-0 | |
| Sat 06.02.99 | 14:00 | West Ham United | 0-4 | Arsenal | 0-2 | |
| Sat 06.02.99 | 14:00 | Tottenham Hotspur | 0-0 | Coventry City | 0-0 | |
| Sat 06.02.99 | 14:00 | Liverpool | 3-1 | Middlesbrough | 3-0 | |
| Sat 06.02.99 | 14:00 | Nottingham Forest | 1-8 | Manchester United | 1-2 | |
| Sat 06.02.99 | 14:00 | Leicester City | 0-2 | Sheffield Wednesday | 0-0 | |
| Sun 07.02.99 | 15:00 | Derby County | 2-1 | Everton | 0-1 | |
| Mon 08.02.99 | 19:00 | Charlton Athletic | 2-0 | Wimbledon | 1-0 | |
| Round 25. | ||||||
| Sat 13.02.99 | 14:00 | West Ham United | 2-1 | Nottingham Forest | 2-0 | |
| Sat 13.02.99 | 14:00 | Charlton Athletic | 1-0 | Liverpool | 0-0 | |
| Wed 17.02.99 | 18:45 | Chelsea | 1-1 | Blackburn Rovers | 1-0 | |
| Wed 17.02.99 | 18:45 | Everton | 5-0 | Middlesbrough | 2-0 | |
| Wed 17.02.99 | 19:00 | Aston Villa | 1-2 | Leeds United | 0-2 | |
| Wed 17.02.99 | 19:00 | Newcastle United | 4-1 | Coventry City | 1-1 | |
| Wed 17.02.99 | 19:00 | Manchester United | 1-1 | Arsenal | 0-0 | |
| Tue 02.03.99 | 18:45 | Tottenham Hotspur | 3-0 | Southampton | 1-0 | |
| Wed 03.03.99 | 19:00 | Sheffield Wednesday | 1-2 | Wimbledon | 0-2 | |
| Wed 05.05.99 | 18:45 | Leicester City | 1-2 | Derby County | 1-1 | |
| Round 26. | ||||||
| Sat 20.02.99 | 14:00 | Liverpool | 2-2 | West Ham United | 2-1 | |
| Sat 20.02.99 | 14:00 | Leeds United | 1-0 | Everton | 0-0 | |
| Sat 20.02.99 | 14:00 | Derby County | 0-2 | Charlton Athletic | 0-0 | |
| Sat 20.02.99 | 14:00 | Coventry City | 0-1 | Manchester United | 0-0 | |
| Sat 20.02.99 | 14:00 | Blackburn Rovers | 1-4 | Sheffield Wednesday | 0-3 | |
| Sat 20.02.99 | 14:00 | Arsenal | 5-0 | Leicester City | 4-0 | |
| Sat 20.02.99 | 14:00 | Middlesbrough | 0-0 | Tottenham Hotspur | 0-0 | |
| Sat 20.02.99 | 14:00 | Nottingham Forest | 1-3 | Chelsea | 1-2 | |
| Sat 20.02.99 | 14:00 | Southampton | 2-1 | Newcastle United | 2-0 | |
| Sun 21.02.99 | 15:00 | Wimbledon | 0-0 | Aston Villa | 0-0 | |
| Round 27. | ||||||
| Sat 27.02.99 | 14:00 | Chelsea | 2-1 | Liverpool | 2-0 | |
| Sat 27.02.99 | 14:00 | Manchester United | 2-1 | Southampton | 0-0 | |
| Sat 27.02.99 | 14:00 | Charlton Athletic | 0-0 | Nottingham Forest | 0-0 | |
| Sat 27.02.99 | 14:00 | Aston Villa | 1-4 | Coventry City | 0-1 | |
| Sat 27.02.99 | 14:00 | Sheffield Wednesday | 3-1 | Middlesbrough | 1-0 | |
| Sat 27.02.99 | 14:00 | West Ham United | 2-0 | Blackburn Rovers | 2-0 | |
| Sat 27.02.99 | 14:00 | Tottenham Hotspur | 1-1 | Derby County | 0-0 | |
| Sat 27.02.99 | 14:00 | Everton | 1-1 | Wimbledon | 0-1 | |
| Sun 28.02.99 | 15:00 | Newcastle United | 1-1 | Arsenal | 0-1 | |
| Mon 01.03.99 | 19:00 | Leicester City | 1-2 | Leeds United | 0-1 | |
| Round 28. | ||||||
| Sat 06.03.99 | 14:00 | Wimbledon | 0-1 | Leicester City | 0-1 | |
| Sat 06.03.99 | 14:00 | Southampton | 1-0 | West Ham United | 1-0 | |
| Sat 06.03.99 | 14:00 | Coventry City | 2-1 | Charlton Athletic | 0-0 | |
| Tue 09.03.99 | 18:45 | Arsenal | 3-0 | Sheffield Wednesday | 0-0 | |
| Wed 10.03.99 | 18:45 | Nottingham Forest | 1-2 | Newcastle United | 1-1 | |
| Wed 10.03.99 | 19:00 | Derby County | 2-1 | Aston Villa | 2-1 | |
| Wed 10.03.99 | 19:00 | Leeds United | 2-0 | Tottenham Hotspur | 1-0 | |
| Wed 10.03.99 | 19:00 | Blackburn Rovers | 1-2 | Everton | 1-1 | |
| Wed 14.04.99 | 19:00 | Middlesbrough | 0-0 | Chelsea | 0-0 | |
| Wed 05.05.99 | 18:45 | Liverpool | 2-2 | Manchester United | 0-1 | |
| Round 29. | ||||||
| Sat 13.03.99 | 14:00 | Newcastle United | 1-2 | Manchester United | 1-1 | |
| Sat 13.03.99 | 14:00 | Everton | 0-2 | Arsenal | 0-1 | |
| Sat 13.03.99 | 14:00 | Sheffield Wednesday | 0-2 | Leeds United | 0-1 | |
| Sat 13.03.99 | 14:00 | Tottenham Hotspur | 1-0 | Aston Villa | 0-0 | |
| Sat 13.03.99 | 14:00 | Wimbledon | 1-3 | Nottingham Forest | 0-1 | |
| Sat 13.03.99 | 14:00 | Leicester City | 1-1 | Charlton Athletic | 0-0 | |
| Sat 13.03.99 | 14:00 | Derby County | 3-2 | Liverpool | 2-1 | |
| Sat 13.03.99 | 14:00 | Coventry City | 1-1 | Blackburn Rovers | 1-0 | |
| Sat 13.03.99 | 14:00 | Chelsea | 0-1 | West Ham United | 0-0 | |
| Sun 14.03.99 | 15:00 | Middlesbrough | 3-0 | Southampton | 2-0 | |
| Round 30. | ||||||
| Sat 20.03.99 | 14:00 | Arsenal | 2-0 | Coventry City | 1-0 | |
| Sat 20.03.99 | 14:00 | Blackburn Rovers | 3-1 | Wimbledon | 3-0 | |
| Sat 20.03.99 | 14:00 | Leeds United | 4-1 | Derby County | 3-1 | |
| Sat 20.03.99 | 14:00 | Nottingham Forest | 1-2 | Middlesbrough | 1-1 | |
| Sat 20.03.99 | 14:00 | Southampton | 1-0 | Sheffield Wednesday | 1-0 | |
| Sat 20.03.99 | 14:00 | West Ham United | 2-0 | Newcastle United | 1-0 | |
| Sun 21.03.99 | 15:00 | Aston Villa | 0-3 | Chelsea | 0-0 | |
| Sun 21.03.99 | 15:00 | Manchester United | 3-1 | Everton | 0-0 | |
| Tue 20.04.99 | 18:45 | Charlton Athletic | 1-4 | Tottenham Hotspur | 1-0 | |
| Wed 21.04.99 | 19:00 | Liverpool | 0-1 | Leicester City | 0-0 | |
| Round 31. | ||||||
| Fri 02.04.99 | 17:00 | Aston Villa | 0-0 | West Ham United | 0-0 | |
| Sat 03.04.99 | 14:00 | Blackburn Rovers | 0-0 | Middlesbrough | 0-0 | |
| Sat 03.04.99 | 14:00 | Charlton Athletic | 0-1 | Chelsea | 0-1 | |
| Sat 03.04.99 | 14:00 | Derby County | 3-4 | Newcastle United | 2-3 | |
| Sat 03.04.99 | 14:00 | Leeds United | 3-1 | Nottingham Forest | 1-0 | |
| Sat 03.04.99 | 14:00 | Liverpool | 3-2 | Everton | 2-1 | |
| Sat 03.04.99 | 14:00 | Sheffield Wednesday | 1-2 | Coventry City | 0-1 | |
| Sat 03.04.99 | 14:00 | Wimbledon | 1-1 | Manchester United | 1-1 | |
| Sat 03.04.99 | 14:00 | Southampton | 0-0 | Arsenal | 0-0 | |
| Sat 03.04.99 | 14:00 | Tottenham Hotspur | 0-2 | Leicester City | 0-1 | |
| Round 32. | ||||||
| Wed 03.02.99 | 19:00 | Manchester United | 1-0 | Derby County | 0-0 | |
| Mon 05.04.99 | 15:00 | Middlesbrough | 3-1 | Wimbledon | 3-0 | |
| Mon 05.04.99 | 15:00 | Newcastle United | 1-1 | Tottenham Hotspur | 0-0 | |
| Mon 05.04.99 | 15:00 | Coventry City | 1-0 | Southampton | 0-0 | |
| Mon 05.04.99 | 15:00 | Everton | 1-2 | Sheffield Wednesday | 1-0 | |
| Mon 05.04.99 | 15:00 | West Ham United | 0-1 | Charlton Athletic | 0-0 | |
| Mon 05.04.99 | 15:00 | Nottingham Forest | 2-2 | Liverpool | 0-1 | |
| Tue 06.04.99 | 18:45 | Leicester City | 2-2 | Aston Villa | 0-1 | |
| Tue 06.04.99 | 18:45 | Arsenal | 1-0 | Blackburn Rovers | 1-0 | |
| Wed 05.05.99 | 18:45 | Chelsea | 1-0 | Leeds United | 0-0 | |
| Round 33. | ||||||
| Sat 10.04.99 | 14:00 | Aston Villa | 3-0 | Southampton | 1-0 | |
| Sat 10.04.99 | 14:00 | Derby County | 1-0 | Nottingham Forest | 0-0 | |
| Sat 10.04.99 | 14:00 | Leicester City | 0-0 | West Ham United | 0-0 | |
| Sat 10.04.99 | 14:00 | Middlesbrough | 2-0 | Charlton Athletic | 1-0 | |
| Sun 11.04.99 | 15:00 | Everton | 2-0 | Coventry City | 1-0 | |
| Sun 11.04.99 | 15:00 | Wimbledon | 1-2 | Chelsea | 0-1 | |
| Mon 12.04.99 | 19:00 | Leeds United | 0-0 | Liverpool | 0-0 | |
| Wed 21.04.99 | 19:00 | Sheffield Wednesday | 1-1 | Newcastle United | 0-1 | |
| Wed 05.05.99 | 18:45 | Tottenham Hotspur | 1-3 | Arsenal | 1-2 | |
| Wed 12.05.99 | 19:00 | Blackburn Rovers | 0-0 | Manchester United | 0-0 | |
| Round 34. | ||||||
| Sat 17.04.99 | 10:30 | West Ham United | 5-1 | Derby County | 2-0 | |
| Sat 17.04.99 | 14:00 | Charlton Athletic | 1-1 | Leeds United | 1-1 | |
| Sat 17.04.99 | 14:00 | Coventry City | 1-2 | Middlesbrough | 0-0 | |
| Sat 17.04.99 | 14:00 | Liverpool | 0-1 | Aston Villa | 0-1 | |
| Sat 17.04.99 | 14:00 | Manchester United | 3-0 | Sheffield Wednesday | 2-0 | |
| Sat 17.04.99 | 14:00 | Newcastle United | 1-3 | Everton | 0-2 | |
| Sat 17.04.99 | 14:00 | Nottingham Forest | 0-1 | Tottenham Hotspur | 0-0 | |
| Sat 17.04.99 | 14:00 | Southampton | 3-3 | Blackburn Rovers | 1-2 | |
| Sun 18.04.99 | 15:00 | Chelsea | 2-2 | Leicester City | 1-0 | |
| Mon 19.04.99 | 19:00 | Arsenal | 5-1 | Wimbledon | 1-0 | |
| Round 35. | ||||||
| Sat 24.04.99 | 14:00 | Middlesbrough | 1-6 | Arsenal | 0-3 | |
| Sat 24.04.99 | 14:00 | Wimbledon | 1-1 | Newcastle United | 1-1 | |
| Sat 24.04.99 | 14:00 | Tottenham Hotspur | 1-2 | West Ham United | 0-1 | |
| Sat 24.04.99 | 14:00 | Blackburn Rovers | 1-3 | Liverpool | 0-3 | |
| Sat 24.04.99 | 14:00 | Everton | 4-1 | Charlton Athletic | 2-0 | |
| Sat 24.04.99 | 14:00 | Aston Villa | 2-0 | Nottingham Forest | 1-0 | |
| Sat 24.04.99 | 14:00 | Leicester City | 1-0 | Coventry City | 1-0 | |
| Sat 24.04.99 | 14:00 | Derby County | 0-0 | Southampton | 0-0 | |
| Sun 25.04.99 | 14:00 | Sheffield Wednesday | 0-0 | Chelsea | 0-0 | |
| Sun 25.04.99 | 15:00 | Leeds United | 1-1 | Manchester United | 1-0 | |
| Round 36. | ||||||
| Sat 01.05.99 | 14:00 | Newcastle United | 1-1 | Middlesbrough | 0-0 | |
| Sat 01.05.99 | 14:00 | Manchester United | 2-1 | Aston Villa | 1-1 | |
| Sat 01.05.99 | 14:00 | Charlton Athletic | 0-0 | Blackburn Rovers | 0-0 | |
| Sat 01.05.99 | 14:00 | West Ham United | 1-5 | Leeds United | 0-2 | |
| Sat 01.05.99 | 14:00 | Southampton | 2-1 | Leicester City | 1-1 | |
| Sat 01.05.99 | 14:00 | Nottingham Forest | 2-0 | Sheffield Wednesday | 2-0 | |
| Sat 01.05.99 | 14:00 | Chelsea | 3-1 | Everton | 1-0 | |
| Sat 01.05.99 | 14:00 | Coventry City | 2-1 | Wimbledon | 2-0 | |
| Sat 01.05.99 | 14:00 | Liverpool | 3-2 | Tottenham Hotspur | 0-2 | |
| Sun 02.05.99 | 15:00 | Arsenal | 1-0 | Derby County | 1-0 | |
| Round 37. | ||||||
| Sat 08.05.99 | 14:00 | Aston Villa | 3-4 | Charlton Athletic | 1-1 | |
| Sat 08.05.99 | 14:00 | Derby County | 0-0 | Coventry City | 0-0 | |
| Sat 08.05.99 | 14:00 | Wimbledon | 0-2 | Southampton | 0-0 | |
| Sat 08.05.99 | 14:00 | Sheffield Wednesday | 1-0 | Liverpool | 0-0 | |
| Sat 08.05.99 | 14:00 | Leicester City | 2-0 | Newcastle United | 2-0 | |
| Sat 08.05.99 | 14:00 | Everton | 6-0 | West Ham United | 3-0 | |
| Sat 08.05.99 | 14:00 | Blackburn Rovers | 1-2 | Nottingham Forest | 1-1 | |
| Sun 09.05.99 | 15:00 | Middlesbrough | 0-1 | Manchester United | 0-1 | |
| Mon 10.05.99 | 19:00 | Tottenham Hotspur | 2-2 | Chelsea | 1-1 | |
| Tue 11.05.99 | 18:45 | Leeds United | 1-0 | Arsenal | 0-0 | |
| Round 38. | ||||||
| Sun 16.05.99 | 14:00 | Manchester United | 2-1 | Tottenham Hotspur | 1-1 | |
| Sun 16.05.99 | 14:00 | Coventry City | 2-2 | Leeds United | 0-1 | |
| Sun 16.05.99 | 14:00 | Arsenal | 1-0 | Aston Villa | 0-0 | |
| Sun 16.05.99 | 14:00 | Chelsea | 2-1 | Derby County | 1-0 | |
| Sun 16.05.99 | 14:00 | West Ham United | 4-0 | Middlesbrough | 2-0 | |
| Sun 16.05.99 | 14:00 | Charlton Athletic | 0-1 | Sheffield Wednesday | 0-0 | |
| Sun 16.05.99 | 14:00 | Liverpool | 3-0 | Wimbledon | 1-0 | |
| Sun 16.05.99 | 14:00 | Newcastle United | 1-1 | Blackburn Rovers | 0-1 | |
| Sun 16.05.99 | 14:00 | Southampton | 2-0 | Everton | 1-0 | |
| Sun 16.05.99 | 14:00 | Nottingham Forest | 1-0 | Leicester City | 0-0 | |
Prepared and maintained by Todor Krastev
todor1966@yahoo.com
Last updated: 16 Mar 2024
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