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| Kick-off time | Match | Match Id. |
Results after: | |||
| CET | Local | 90 Min. | Extra Time | Half Time | ||
Saturday, June 26, 1999 |
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| 15:00 | 16:00 | Trans Narva (EST) - FC Jokerit (FIN) | 20 | 1 - 4 | 0 - 3 | |
| 15:00 | 18:00 | FC Ararat (ARM) - FCM Bacau (ROM) | 7 | 1 - 0 | 0 - 0 | |
| 16:00 | 15:00 | Newry Town FC (NIR) - NK Hrvatski Dragovoljac (CRO) | 13 | 2 - 0 | 1 - 0 | |
| 16:00 | 18:00 | FC Kolkheti-1913 (GEO) - FC Cementarnica 55 (MKD) | 15 | 0 - 4 | 0 - 3 | |
| 16:00 | 19:00 | FC Karabakh Agdam (AZE) - Maccabi Haifa (ISR) | 14 | 0 - 1 | 0 - 1 | |
| 17:00 | 17:00 | Floriana FC (MLT) - Aberystwyth Town FC (WAL) | 18 | 2 - 1 | 2 - 1 | |
| 17:00 | 18:00 | FK Ventspils (LAT) - Valerenga Fotball (NOR) | 1 | 2 - 0 | 1 - 0 | |
| 17:00 | 18:00 | Tiligul Tiraspol (MOL) - KP Polonia Warszawa (POL) | 3 | 0 - 0 | 0 - 0 | |
| 17:30 | 17:30 | FK Ozeta Dukla Trencin (SVK) - FC Pobeda (MKD) | 4 | 3 - 1 | 3 - 1* | 2 - 0 |
| *FC Pobeda won 4-3 on penalty kicks | ||||||
| 17:30 | 17:30 | MSK Zilina (SVK) - Herfolge Boldklub (DEN) | 6 | 2 - 0 | 1 - 0 | |
| 17:30 | 17:30 | FC Basel (SWI) - NK Prevalje Korotan (SLO) | 16 | 6 - 0 | 4 - 0 | |
| 18:00 | 18:00 | Teuta FC (ALB) - IA-Akranes (ISL) | 19 | 2 - 1 | 0 - 1 | |
| 19:00 | 19:00 | Vasas Budapest (HUN) - Union Sportive Luxembourg (LUX) | 9 | 4 - 0 | 1 - 0 | |
| 20:00 | 19:00 | Gotu Itrottarfelag (FAR) - NK Jedinstvo (BHZ) | 17 | 1 - 0 | 0 - 0 | |
| 20:00 | 20:00 | NK Varteks (CRO) - Lokomotiv-96 Vitebsk (BLS) | 8 | 2 - 2 | 0 - 1 | |
| 20:00 | 20:00 | K. St.-Truidense VV (BEL) - FC Spartak Varna (BUL) | 2 | 6 - 0 | 4 - 0 | |
| Sunday, June 27, 1999 | ||||||
| 17:00 | 17:00 | Halmstads BK (SWE) - NK Rudar Velenje (SLO) | 5 | 2 - 2 | 2 - 1 | |
| 17:00 | 18:00 | FC Gomel (BLS) - SK Hradec Kralove (CZE) | 12 | 1 - 0 | 1 - 0* | 1 - 0 |
| *FC Gomel won 2-1 on penalty kicks | ||||||
| 17:30 | 17:30 | FK Ekranas Panevezys (LIT) - FC Ceahlaul Piatra Neamt (ROM) | 11 | 0 - 1 | 0 - 1 | |
| 18:00 | 18:00 | Neuchâtel Xamax (SWI) - Shelbourne FC (IRL) | 10 | 2 - 0 | 0 - 0 | |
CET = Central European Time
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