| Tuesday 13th July 1999 | |||
| 1st Leg | |||
| IBV Vestmannaeyjar | 1-0 | SK Tirana | |
| Wednesday 14th July 1999 | |||
| 1st Leg | |||
| Barry Town | 0-0 | Valletta | |
| HB Torshavn | 1-1 | FC Haka Valkeakoski | |
| Jeunesse Esch | 0-2 | Skonto Riga | |
| Liteks Lovech | 3-0 | Glentoran | |
| Partizan Belgrade | 6-0 | Flora Tallinn | |
| Sloga Jug'nat Skopje | 1-0 | Kapaz Ganja | |
| St Patrick's Ath | 0-5 | Zimbru Chisinau | |
| Zhalgiris Vilnius | 2-0 | Tsement Ararat | |
| Wednesday 21st July 1999 | |||
| 2nd Leg | |||
| FC Haka Valkeakoski | 6-0 | HB Torshavn | (7-1) |
| Flora Tallinn | 1-4 | Partizan Belgrade | (1-10) |
| Glentoran | 0-2 | Liteks Lovech | (0-5) |
| Kapaz Ganja | 2-1 | Sloga Jug'nat Skopje | (2-2) |
| (Sloga Jug'nat Skopje won on away goals) | |||
| SK Tirana | 1-2 | IBV Vestmannaeyjar | (1-3) |
| Skonto Riga | 8-0 | Jeunesse Esch | (10-0) |
| Tsement Ararat | 0-3 | Zhalgiris Vilnius | (0-5) |
| Valletta | 3-2 | Barry Town | (3-2) |
| Zimbru Chisinau | 5-0 | St Patrick's Ath | (10-0) |
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
