| Final played at Bulgarska armiya stadium, Sofia. | | date | team 1 | score | team 2 | HT | | Wed 26.05.99 | CSKA Sofia | 1-0 | Litex Lovech | 0-0 | | 1-0 Valenitin Stanchev 82' |
| dates | team 1 | leg 1 | leg 2 | team 2 | HT1 | HT2 | aggr. | | 28.04,12.05 | CSKA Sofia | 1-0 | 2-2 | Levski Kyustendil | --- | --- | 3-2 | | 28.04,12.05 | Lokomotiv Sofia | 0-0 | 0-3 | Litex Lovech | --- | --- | 0-1 |
| dates | team 1 | leg 1 | leg 2 | team 2 | HT1 | HT2 | aggr. | | 10.03,21.04 | CSKA Sofia | 4-1 | 2-1 | Minyor Pernik | --- | --- | 6-2 | | 10.03,21.04 | Spartak Varna | 1-3 | 2-1 | Levski Kyustendil | --- | --- | 4-3 | | 10.03,21.04 | Pirin Blagoevgrad | 0-1 | 2-2 | Lokomotiv Sofia | --- | --- | 2-3 | | 10.03,21.04 | Litex Lovech | 1-0 | 0-1 | Slavia Sofia | --- | --- | 1-1 4-2p |
| dates | team 1 | leg 1 | leg 2 | team 2 | HT1 | HT2 | aggr. | | 28.11,09.12 | CSKA Sofia | 2-0 | 1-2 | Septemvri Sofia | --- | --- | 3-2 | | 28.11,09.12 | Lokomotiv Plovdiv | 3-3 | 0-6 | Minyor Pernik | --- | --- | 3-9 | | 28.11,09.12 | Dobrudzha Dobrich | 1-2 | 0-2 | Levski Kyustendil | --- | --- | 1-4 | | 28.11,09.12 | Shumen | 2-2 | 0-6 | Spartak Varna | --- | --- | 2-8 | | 28.11,09.12 | Pirin Blagoevgrad | 3-0 | 2-3 | Neftohimik Burgas | --- | --- | 5-3 | | 28.11,09.12 | Lokomotiv Sofia | 4-2 | 2-1 | Botev Plovdiv | --- | --- | 6-3 | | 28.11,09.12 | Levski Sofia | 2-0 | 0-3 | Slavia Sofia | --- | --- | 2-3 | | 28.11,09.12 | Metalurg Pernik | 2-1 | 1-3 | Litex Lovech | --- | --- | 3-4 |
| date | team 1 | score | team 2 | HT | aggr. | | Sat 31.10.98 | Etar Veliko Tarnovo | 0-2 | CSKA Sofia | --- | | | Sat 31.10.98 | Planinets Apriltsi | 1-1 | Septemvri Sofia | --- | 2-4p | | Sat 31.10.98 | Marek Dupnitsa | 1-2 | Minyor Pernik | --- | aet | | Sat 31.10.98 | Vidima-Rakovski Sevlievo | 2-3 | Lokomotiv Plovdiv | --- | aet | | Sat 31.10.98 | Maritsa Plovdiv | 0-3 | Levski Kyustendil | --- | | | Sat 31.10.98 | Lovico Suhindol | 2-3 | Dobrudzha Dobrich | --- | aet | | Sat 31.10.98 | Strumska Slava Radomir | 0-3 | Spartak Varna | --- | | | Sat 31.10.98 | Botev Vratsa | 1-5 | Shumen | --- | | | Sat 31.10.98 | Neftohimik Burgas | 3-1 | Kremikovtsi | --- | | | Sat 31.10.98 | Pirin Blagoevgrad | 2-1 | Akademik Sofia | --- | | | Sat 31.10.98 | Kalikra Kavarna | 0-0 | Botev Plovdiv | --- | | | Sat 31.10.98 | Spartak Plovdiv | 0-2 | Lokomotiv Sofia | --- | | | Sat 31.10.98 | Dimitrovgrad | 0-2 | Slavia Sofia | --- | | | Sat 31.10.98 | Levski Sofia | 4-0 | Belasitsa Petrich | --- | | | Sat 31.10.98 | Metalurg Pernik | 1-0 | Chardafon Gabrovo | --- | | | Sat 31.10.98 | Rodopa Smolyan | 1-3 | Litex Lovech | --- | |
| date | team 1 | score | team 2 | HT | aggr. | | Tue 13.10.98 | Hebar Pazardzhik | 0-1 | Etar Veliko Tarnovo | --- | | | Tue 13.10.98 | Planinets Apriltsi | 1-0 | Chernomorets Burgas | --- | | | Tue 13.10.98 | Marek Dupnitsa | 2-0 | Svetkavitsa Turgoviste | --- | | | Tue 13.10.98 | Vidima-Rakovski Sevlievo | 2-0 | Olympic Sliven | --- | | | Tue 13.10.98 | Devnya | 1-2 | Maritsa Plovdiv | --- | | | Tue 13.10.98 | Lovico Suhindol | 3-1 | Haskovo | --- | | | Tue 13.10.98 | Strumska Slava Radomir | 1-0 | Cherno More Varna | --- | | | Tue 13.10.98 | Bdin Vidin | 0-0 | Botev Vratsa | --- | 3-4p | | Tue 13.10.98 | Port Burgas | 0-4 | Kremikovtsi | --- | | | Tue 13.10.98 | Satelit Stara Zagora | 0-4 | Akademik Sofia | --- | | | Tue 13.10.98 | Kalikra Kavarna | 1-0 | Spartak Pleven | --- | | | Tue 13.10.98 | Spartak Plovdiv | 1-0 | Antibiotic Razgrad | --- | | | Tue 13.10.98 | Dzhebel | 0-1 | Dimitrovgrad | --- | | | Tue 13.10.98 | Perun Kresna | 0-2 | Belasitsa Petrich | --- | | | Tue 13.10.98 | Yambol | 0-0 | Chardafon Gabrovo | --- | 2-3p | | Tue 13.10.98 | Rodopa Smolyan | 1-0 | Olympic Teteven | --- | |
| date | team 1 | score | team 2 | HT | aggr. |
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| CSKA Sofia played in Europe_Cups Men UEFA 2000 and was eliminated in Round 1 by Newcastle United. | | CSKA Sofia was 5th in A grupa 1999, Litex Lovech was Champion. |
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