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| 01.10.1999 | 20:45 | Nottingham Forest | - | Barnsley FC | 3:0 (0:0) | |
| 02.10.1999 | 16:00 | Charlton Athletic | - | Birmingham City | 1:0 (1:0) | |
| 16:00 | Crystal Palace | - | Portsmouth FC | 4:0 (1:0) | ||
| 16:00 | Grimsby Town | - | Ipswich Town | 2:1 (1:0) | ||
| 16:00 | Huddersfield Town | - | Sheffield United | 4:1 (2:0) | ||
| 16:00 | Manchester City | - | Port Vale FC | 2:1 (2:0) | ||
| 16:00 | Norwich City | - | Fulham FC | 1:2 (1:0) | ||
| 16:00 | Queens Park Rangers | - | Blackburn Rovers | 0:0 (0:0) | ||
| 16:00 | Swindon Town | - | Bolton Wanderers | 0:4 (0:4) | ||
| 16:00 | Walsall FC | - | Stockport County | 1:2 (0:1) | ||
| 03.10.1999 | 14:00 | Crewe Alexandra | - | Tranmere Rovers | 0:2 (0:0) | |
| 14:00 | Wolverhampton Wanderers | - | West Bromwich Albion | 1:1 (1:0) |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Charlton Athletic | 10 | 8 | 1 | 1 | 21:9 | 12 | 25 |
| 2 |
|
Fulham FC | 10 | 6 | 4 | 0 | 14:5 | 9 | 22 |
| 3 |
|
Huddersfield Town | 10 | 6 | 1 | 3 | 22:13 | 9 | 19 |
| 4 |
|
Manchester City | 10 | 6 | 1 | 3 | 14:6 | 8 | 19 |
| 5 |
|
Birmingham City | 10 | 5 | 3 | 2 | 19:12 | 7 | 18 |
| 6 |
|
Ipswich Town | 10 | 5 | 2 | 3 | 21:13 | 8 | 17 |
| 7 |
|
Stockport County | 10 | 5 | 2 | 3 | 14:15 | -1 | 17 |
| 8 |
|
Barnsley FC | 10 | 5 | 1 | 4 | 23:21 | 2 | 16 |
| 9 |
|
Blackburn Rovers | 10 | 4 | 3 | 3 | 15:10 | 5 | 15 |
| 10 |
|
Grimsby Town | 10 | 4 | 2 | 4 | 10:13 | -3 | 14 |
| 11 |
|
Nottingham Forest | 10 | 3 | 4 | 3 | 15:12 | 3 | 13 |
| 12 |
|
Queens Park Rangers | 10 | 3 | 4 | 3 | 15:14 | 1 | 13 |
| 13 |
|
West Bromwich Albion | 10 | 2 | 7 | 1 | 10:10 | 0 | 13 |
| 14 |
|
Bolton Wanderers | 10 | 3 | 3 | 4 | 16:15 | 1 | 12 |
| 15 |
|
Crystal Palace | 10 | 3 | 3 | 4 | 16:18 | -2 | 12 |
| 16 |
|
Portsmouth FC | 10 | 3 | 3 | 4 | 11:17 | -6 | 12 |
| 17 |
|
Crewe Alexandra | 10 | 3 | 2 | 5 | 12:18 | -6 | 11 |
| 18 |
|
Sheffield United | 10 | 3 | 2 | 5 | 15:22 | -7 | 11 |
| 19 |
|
Port Vale FC | 10 | 3 | 1 | 6 | 12:15 | -3 | 10 |
| 20 |
|
Norwich City | 10 | 2 | 3 | 5 | 9:13 | -4 | 9 |
| 21 |
|
Wolverhampton Wanderers | 10 | 1 | 5 | 4 | 9:14 | -5 | 8 |
| 22 |
|
Tranmere Rovers | 10 | 2 | 2 | 6 | 9:17 | -8 | 8 |
| 23 |
|
Swindon Town | 10 | 2 | 2 | 6 | 7:17 | -10 | 8 |
| 24 |
|
Walsall FC | 10 | 1 | 3 | 6 | 8:18 | -10 | 6 |
| Promotion | |
| Relégation |
