| Sunday 5th September 1999 | |||
| English Division OneTable » | |||
| Bolton Wanderers | 3-3 | Birmingham City | |
| Port Vale | 3-1 | Grimsby Town | |
| English Division ThreeTable » | |||
| Barnet | 2-1 | Macclesfield Town | |
| Plymouth Argyle | 3-3 | Brighton and Hove A | |
| Scottish Division TwoTable » | |||
| Hamilton Academical | 1-1 | Stenhousemuir | |
| European Championships Qualifying Round Group 6 | |||
| Cyprus | 3-2 | Israel | |
| European Championships Qualifying Round Group 8 | |||
| Yugoslavia | 3-1 | FYR Macedonia | |
| Republic of Ireland Premier DivisionTable » | |||
| Derry City | 1-0 | Shamrock Rovers | |
» Results : Sunday 5th September 1999
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