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| I | Shakhtar Donetsk | - | Sileks Kratovo | 3:1 (0:0) | ||
| V | Sileks Kratovo | - | Shakhtar Donetsk | 2:1 (1:1) | ||
| I: 10.08.1999 18:00 | V: 26.08.1999 16:30 | Campeones: Shakhtar Donetsk | ||||
| I | HJK Helsinki | - | Shirak FC | 2:0 (1:0) | ||
| V | Shirak FC | - | HJK Helsinki | 1:0 (1:0) | ||
| I: 11.08.1999 18:00 | V: 26.08.1999 15:00 | Campeones: HJK Helsinki | ||||
| I | FK Yerevan | - | Hapoel Tel Aviv | 0:2 (0:0) | ||
| V | Hapoel Tel Aviv | - | FK Yerevan | 2:1 (0:0) | ||
| I: 12.08.1999 16:00 | V: 26.08.1999 19:15 | Campeones: Hapoel Tel Aviv | ||||
| I | Neftçi PFK | - | Crvena Zvezda | 2:3 (1:0) | ||
| V | Crvena Zvezda | - | Neftçi PFK | 1:0 (0:0) | ||
| I: 12.08.1999 16:00 | V: 26.08.1999 18:00 | Campeones: Crvena Zvezda | ||||
| I | FC Sheriff | - | Sigma Olomouc | 1:1 (1:1) | ||
| V | Sigma Olomouc | - | FC Sheriff | 0:0 (0:0) | ||
| I: 12.08.1999 16:00 | V: 26.08.1999 20:00 | Campeones: Sigma Olomouc | ||||
| I | Lokomotiv Tbilisi | - | Linfield FC | 1:0 (1:0) | ||
| V | Linfield FC | - | Lokomotiv Tbilisi | 1:1 (0:0) | ||
| I: 12.08.1999 16:00 | V: 26.08.1999 20:30 | Campeones: Lokomotiv Tbilisi | ||||
| I | FK Liepājas Metalurgs | - | Lech Poznań | 3:2 (1:1) | ||
| V | Lech Poznań | - | FK Liepājas Metalurgs | 3:1 (0:0) | ||
| I: 12.08.1999 16:30 | V: 26.08.1999 18:00 | Campeones: Lech Poznań | ||||
| I | BATE Borisov | - | Lokomotiv Moskva | 1:7 (0:3) | ||
| V | Lokomotiv Moskva | - | BATE Borisov | 5:0 (3:0) | ||
| I: 12.08.1999 17:00 | V: 25.08.1999 17:00 | Campeones: Lokomotiv Moskva | ||||
| I | Lantana Tallinn | - | Torpedo Kutaisi | 0:5 (0:3) | ||
| V | Torpedo Kutaisi | - | Lantana Tallinn | 4:2 (3:1) | ||
| I: 12.08.1999 17:00 | V: 26.08.1999 14:30 | Campeones: Torpedo Kutaisi | ||||
| I | FK Vllaznia | - | Spartak Trnava | 1:1 (1:1) | ||
| V | Spartak Trnava | - | FK Vllaznia | 2:0 (0:0) | ||
| I: 12.08.1999 17:00 | V: 26.08.1999 19:00 | Campeones: Spartak Trnava | ||||
| I | ND HIT Gorica | - | UWIC Inter Cardiff | 2:0 (0:0) | ||
| V | UWIC Inter Cardiff | - | ND HIT Gorica | 1:0 (0:0) | ||
| I: 12.08.1999 17:00 | V: 26.08.1999 20:30 | Campeones: ND HIT Gorica | ||||
| I | Maccabi Tel Aviv | - | Zalgiris Kaunas | 3:1 (2:1) | ||
| V | Zalgiris Kaunas | - | Maccabi Tel Aviv | 2:1 (1:0) | ||
| I: 12.08.1999 17:30 | V: 26.08.1999 17:00 | Campeones: Maccabi Tel Aviv | ||||
| I | KÍ Klaksvík | - | Grazer AK | 0:5 (0:3) | ||
| V | Grazer AK | - | KÍ Klaksvík | 4:0 (0:0) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 18:00 | Campeones: Grazer AK | ||||
| I | FK Bodø/Glimt | - | FC Vaduz | 1:0 (1:0) | ||
| V | FC Vaduz | - | FK Bodø/Glimt | 1:2 (1:1) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 19:00 | Campeones: FK Bodø/Glimt | ||||
| I | Belshina Bobruisk | - | Omonia Nikosia | 1:5 (1:3) | ||
| V | Omonia Nikosia | - | Belshina Bobruisk | 3:0 (0:0) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 19:15 | Campeones: Omonia Nikosia | ||||
| I | FK Rīga | - | Helsingborgs IF | 0:0 (0:0) | ||
| V | Helsingborgs IF | - | FK Rīga | 5:0 (3:0) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 19:00 | Campeones: Helsingborgs IF | ||||
| I | FK Krivbas (old) | - | Shamkir FK | 3:0 (1:0) | ||
| V | Shamkir FK | - | FK Krivbas (old) | 0:2 (0:1) | ||
| I: 12.08.1999 18:00 | V: 24.08.1999 16:00 | Campeones: FK Krivbas (old) | ||||
| I | Tulevik Viljandi | - | Club Brugge KV | 0:3 (0:0) | ||
| V | Club Brugge KV | - | Tulevik Viljandi | 2:0 (0:0) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 20:30 | Campeones: Club Brugge KV | ||||
| I | Vojvodina | - | Újpest FC | 4:0 (2:0) | ||
| V | Újpest FC | - | Vojvodina | 1:1 (0:0) | ||
| I: 12.08.1999 18:00 | V: 26.08.1999 20:00 | Campeones: Vojvodina | ||||
| I | Vardar Skopje | - | Legia Warszawa | 0:5 (0:2) | ||
| V | Legia Warszawa | - | Vardar Skopje | 4:0 (2:0) | ||
| I: 12.08.1999 18:30 | V: 26.08.1999 20:00 | Campeones: Legia Warszawa | ||||
| I | Vaasan PS | - | St. Johnstone FC | 1:1 (1:0) | ||
| V | St. Johnstone FC | - | Vaasan PS | 2:0 (0:0) | ||
| I: 12.08.1999 18:30 | V: 26.08.1999 20:45 | Campeones: St. Johnstone FC | ||||
| I | APOEL Nikosia | - | Levski Sofia | 0:0 (0:0) | ||
| V | Levski Sofia | - | APOEL Nikosia | 2:0 (0:0) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 16:30 | Campeones: Levski Sofia | ||||
| I | Ferencvárosi TC | - | Constructorul Chişinău | 3:1 (2:0) | ||
| V | Constructorul Chişinău | - | Ferencvárosi TC | 1:1 (1:1) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 16:00 | Campeones: Ferencvárosi TC | ||||
| I | IFK Göteborg | - | Cork City | 3:0 (1:0) | ||
| V | Cork City | - | IFK Göteborg | 1:0 (1:0) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 19:00 | Campeones: IFK Göteborg | ||||
| I | FK AŠK Inter Slovnaft Bratislava | - | KF Bylis Ballsh | 3:1 (2:0) | ||
| V | KF Bylis Ballsh | - | FK AŠK Inter Slovnaft Bratislava | 0:2 (0:1) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 19:30 | Campeones: FK AŠK Inter Slovnaft Bratislava | ||||
| I | Lyngby FC | - | Birkirkara FC | 7:0 (2:0) | ||
| V | Birkirkara FC | - | Lyngby FC | 0:0 (0:0) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 19:30 | Campeones: Lyngby FC | ||||
| I | Viking FK | - | CE Principat | 7:0 (3:0) | ||
| V | CE Principat | - | Viking FK | 0:11 (0:5) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 21:00 | Campeones: Viking FK | ||||
| I | FC Mondercange | - | Dinamo Bucureşti | 2:6 (1:2) | ||
| V | Dinamo Bucureşti | - | FC Mondercange | 7:0 (4:0) | ||
| I: 12.08.1999 19:00 | V: 26.08.1999 16:00 | Campeones: Dinamo Bucureşti | ||||
| I | Grasshopper Club Zürich | - | Bray Wanderers | 4:0 (1:0) | ||
| V | Bray Wanderers | - | Grasshopper Club Zürich | 0:4 (0:2) | ||
| I: 12.08.1999 19:30 | V: 26.08.1999 20:00 | Campeones: Grasshopper Club Zürich | ||||
| I | Sliema Wanderers | - | FC Zürich | 0:3 (0:1) | ||
| V | FC Zürich | - | Sliema Wanderers | 1:0 (0:0) | ||
| I: 12.08.1999 19:30 | V: 26.08.1999 19:30 | Campeones: FC Zürich | ||||
| I | AFC Steaua București | - | Levadia Maardu | 3:0 (1:0) | ||
| V | Levadia Maardu | - | AFC Steaua București | 1:4 (1:0) | ||
| I: 12.08.1999 19:30 | V: 26.08.1999 17:00 | Campeones: AFC Steaua București | ||||
| I | MKE Ankaragücü | - | B36 Tórshavn | 1:0 (1:0) | ||
| V | B36 Tórshavn | - | MKE Ankaragücü | 0:1 (0:0) | ||
| I: 12.08.1999 19:30 | V: 26.08.1999 19:30 | Campeones: MKE Ankaragücü | ||||
| I | RSC Anderlecht | - | ÍF Leiftur | 6:1 (3:1) | ||
| V | ÍF Leiftur | - | RSC Anderlecht | 0:3 (0:2) | ||
| I: 12.08.1999 20:00 | V: 26.08.1999 19:30 | Campeones: RSC Anderlecht | ||||
| I | Olimpija Ljubljana | - | FK Kareda Siauliai | 1:1 (1:0) | ||
| V | FK Kareda Siauliai | - | Olimpija Ljubljana | 2:2 (0:1) | ||
| I: 12.08.1999 20:00 | V: 26.08.1999 15:30 | Campeones: Olimpija Ljubljana | ||||
| I | Hajduk Split | - | F91 Dudelange | 5:0 (2:0) | ||
| V | F91 Dudelange | - | Hajduk Split | 1:1 (0:0) | ||
| I: 12.08.1999 20:15 | V: 26.08.1999 18:30 | Campeones: Hajduk Split | ||||
| I | Cwmbran Town | - | Celtic FC | 0:6 (0:3) | ||
| V | Celtic FC | - | Cwmbran Town | 4:0 (1:0) | ||
| I: 12.08.1999 20:25 | V: 26.08.1999 20:45 | Campeones: Celtic FC | ||||
| I | Portadown FC | - | CSKA Sofia | 0:3 (0:1) | ||
| V | CSKA Sofia | - | Portadown FC | 5:0 (2:0) | ||
| I: 12.08.1999 20:30 | V: 24.08.1999 19:00 | Campeones: CSKA Sofia | ||||
| I | KR Reykjavík | - | Kilmarnock FC | 1:0 (0:0) | ||
| V | Kilmarnock FC | - | KR Reykjavík | 2:0 (0:0) | ||
| I: 12.08.1999 21:00 | V: 26.08.1999 20:45 | Campeones: Kilmarnock FC | ||||
