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