| Wednesday 22nd September 1999 | |||
| English League Cup Second Round 2nd Leg | |||
| Blackburn Rovers | 3-1 | Portsmouth | (6-1) |
| Bristol City | 0-0 | Nottingham Forest | (1-2) |
| Coventry City | 3-1 | Tranmere Rovers | (4-6) |
| Derby County | 3-1 | Swansea City | (3-1) |
| Everton | 0-1 | Oxford United | (1-2) |
| Leicester City | 4-2 | Crystal Palace | (7-5) |
| Reading | 2-2 | Bradford City | aet (3-3) |
| (Bradford City won on away goals) | |||
| Sheffield Wednesday | 3-1 | Stoke City | (3-1) |
| UEFA Champions League First Round Group A | |||
| Lazio | 2-1 | Dinamo Kiev | |
| Maribor Teatanic | 0-2 | Bayer Leverkusen | |
| UEFA Champions League First Round Group B | |||
| Arsenal | 3-1 | AIK Stockholm | |
| Barcelona | 4-2 | Fiorentina | |
| UEFA Champions League First Round Group C | |||
| Borussia Dortmund | 3-1 | Boavista | |
| Rosenborg | 2-2 | Feyenoord | |
| UEFA Champions League First Round Group D | |||
| Croatia Zagreb | 1-2 | Marseille | |
| Sturm Graz | 0-3 | Manchester United | |
| Finnish VeikkausligaTable » | |||
| FC Lahti | 4-3 | TPV Tampere | |
| HJK Helsinki | 2-1 | Inter Turku | |
| MyPa-47 Anjalankoski | 3-1 | RoPS Rovaniemi | |
| TPS Turku | 1-1 | VPS Vaasa | |
» Results : Wednesday 22nd September 1999
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