| Wednesday 28th July 1999 | |||
| 1st Leg | |||
| Anorthosis Famagusta | 2-1 | Slovan Bratislava | |
| Besiktas | 1-1 | Hapoel Haifa | |
| CSKA Moscow | 2-0 | Molde | |
| Dinamo Kiev | 2-0 | Zhalgiris Vilnius | |
| Dinamo Tbilisi | 2-1 | Zimbru Chisinau | |
| Dnepr-Transmash Mog' | 0-1 | AIK Stockholm | |
| FC Haka Valkeakoski | 1-4 | Rangers | |
| IBV Vestmannaeyjar | 0-2 | MTK Budapest | |
| Liteks Lovech | 4-1 | Widzew Lodz | |
| Maribor Teatanic | 5-1 | KAA Gent | |
| Partizan Belgrade | 3-1 | NHK Rijeka | |
| Rapid Bucharest | 3-3 | Skonto Riga | |
| Rapid Vienna | 3-0 | Valletta | |
| Sloga Jug'nat Skopje | 0-1 | Brondby | |
| Wednesday 4th August 1999 | |||
| 2nd Leg | |||
| AIK Stockholm | 2-0 | Dnepr-Transmash Mog' | (3-0) |
| Brondby | 1-0 | Sloga Jug'nat Skopje | (2-0) |
| Hapoel Haifa | 0-0 | Besiktas | (1-1) |
| (Hapoel Haifa won on away goals) | |||
| KAA Gent | 3-0 | Maribor Teatanic | (4-5) |
| Molde | 4-0 | CSKA Moscow | (4-2) |
| MTK Budapest | 3-1 | IBV Vestmannaeyjar | (5-1) |
| NHK Rijeka | 0-3 | Partizan Belgrade | (1-6) |
| Rangers | 3-0 | FC Haka Valkeakoski | (7-1) |
| Skonto Riga | 2-1 | Rapid Bucharest | (5-4) |
| Slovan Bratislava | 1-1 | Anorthosis Famagusta | (2-3) |
| Valletta | 0-2 | Rapid Vienna | (0-5) |
| Widzew Lodz | 4-1 | Liteks Lovech | aet (5-5) |
| (Widzew Lodz won on penalties) | |||
| Zhalgiris Vilnius | 0-1 | Dinamo Kiev | (0-3) |
| Zimbru Chisinau | 2-0 | Dinamo Tbilisi | (3-2) |
July 1999
| Jul | Aug | Sep | Oct | Nov | Dec |
| Jan | Feb | Mar | Apr | May | Jun |
| Mo | Tu | We | Th | Fr | Sa | Su |
| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
- Final
- Semi-Final
- Quarter-Final
- Second Round Group A
- Second Round Group B
- Second Round Group C
- Second Round Group D
- First Round Group A
- First Round Group B
- First Round Group C
- First Round Group D
- First Round Group E
- First Round Group F
- First Round Group G
- First Round Group H
- Third Qualifying Round
- Second Qualifying Round
- First Qualifying Round
