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| 10.09.1999 | 20:45 | Barnsley FC | - | Stockport County | 2:1 (2:0) | |
| 11.09.1999 | 16:00 | Birmingham City | - | West Bromwich Albion | 1:1 (1:0) | |
| 16:00 | Blackburn Rovers | - | Tranmere Rovers | 2:0 (0:0) | ||
| 16:00 | Charlton Athletic | - | Bolton Wanderers | 2:1 (1:1) | ||
| 16:00 | Grimsby Town | - | Walsall FC | 1:0 (0:0) | ||
| 16:00 | Manchester City | - | Crystal Palace | 2:1 (1:1) | ||
| 16:00 | Norwich City | - | Crewe Alexandra | 2:1 (1:1) | ||
| 16:00 | Port Vale FC | - | Fulham FC | 0:2 (0:1) | ||
| 16:00 | Portsmouth FC | - | Ipswich Town | 1:1 (0:0) | ||
| 16:00 | Swindon Town | - | Nottingham Forest | 0:0 (0:0) | ||
| 16:00 | Wolverhampton Wanderers | - | Huddersfield Town | 0:1 (0:0) | ||
| 30.11.1999 | 20:45 | Queens Park Rangers | - | Sheffield United | 3:1 (2:0) |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Charlton Athletic | 7 | 6 | 0 | 1 | 16:6 | 10 | 18 |
| 2 |
|
Ipswich Town | 7 | 4 | 2 | 1 | 18:9 | 9 | 14 |
| 3 |
|
Huddersfield Town | 7 | 4 | 1 | 2 | 15:8 | 7 | 13 |
| 4 |
|
Manchester City | 7 | 4 | 1 | 2 | 10:3 | 7 | 13 |
| 5 |
|
Fulham FC | 7 | 3 | 4 | 0 | 8:4 | 4 | 13 |
| 6 |
|
Birmingham City | 7 | 3 | 3 | 1 | 16:11 | 5 | 12 |
| 7 |
|
Queens Park Rangers | 7 | 3 | 3 | 1 | 15:11 | 4 | 12 |
| 8 |
|
Barnsley FC | 7 | 4 | 0 | 3 | 17:14 | 3 | 12 |
| 9 |
|
Blackburn Rovers | 7 | 3 | 1 | 3 | 11:8 | 3 | 10 |
| 10 |
|
West Bromwich Albion | 7 | 2 | 4 | 1 | 7:7 | 0 | 10 |
| 11 |
|
Stockport County | 7 | 3 | 1 | 3 | 9:12 | -3 | 10 |
| 12 |
|
Nottingham Forest | 7 | 2 | 3 | 2 | 9:8 | 1 | 9 |
| 13 |
|
Portsmouth FC | 7 | 2 | 3 | 2 | 6:9 | -3 | 9 |
| 14 |
|
Crewe Alexandra | 7 | 2 | 2 | 3 | 10:12 | -2 | 8 |
| 15 |
|
Grimsby Town | 7 | 2 | 2 | 3 | 6:8 | -2 | 8 |
|
Norwich City | 7 | 2 | 2 | 3 | 6:8 | -2 | 8 | |
| 17 |
|
Swindon Town | 7 | 2 | 2 | 3 | 6:9 | -3 | 8 |
| 18 |
|
Sheffield United | 7 | 2 | 2 | 3 | 10:16 | -6 | 8 |
| 19 |
|
Port Vale FC | 7 | 2 | 1 | 4 | 9:12 | -3 | 7 |
| 20 |
|
Wolverhampton Wanderers | 7 | 1 | 3 | 3 | 7:9 | -2 | 6 |
| 21 |
|
Walsall FC | 7 | 1 | 3 | 3 | 7:13 | -6 | 6 |
| 22 |
|
Bolton Wanderers | 7 | 1 | 2 | 4 | 7:11 | -4 | 5 |
| 23 |
|
Crystal Palace | 7 | 1 | 2 | 4 | 9:18 | -9 | 5 |
| 24 |
|
Tranmere Rovers | 7 | 1 | 1 | 5 | 3:11 | -8 | 4 |
| Promotion | |
| Relégation |
