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| 26/10/1999 | 19:45 | Crewe Alexandra | - | Fulham FC | 1:1 (1:1) | |
| 19:45 | Crystal Palace | - | West Bromwich Albion | 0:2 (0:2) | ||
| 19:45 | Grimsby Town | - | Portsmouth FC | 1:0 (1:0) | ||
| 19:45 | Huddersfield Town | - | Barnsley FC | 2:1 (1:1) | ||
| 19:45 | Norwich City | - | Stockport County | 2:0 (1:0) | ||
| 19:45 | Swindon Town | - | Port Vale FC | 2:1 (1:1) | ||
| 19:45 | Walsall FC | - | Blackburn Rovers | 1:1 (0:1) | ||
| 19:45 | Wolverhampton Wanderers | - | Sheffield United | 1:0 (0:0) | ||
| 20:00 | Charlton Athletic | - | Tranmere Rovers | 3:2 (0:2) | ||
| 27/10/1999 | 19:45 | Manchester City | - | Ipswich Town | 1:0 (0:0) | |
| 19:45 | Queens Park Rangers | - | Birmingham City | 2:2 (1:0) | ||
| 19:45 | Nottingham Forest | - | Bolton Wanderers | 1:1 (1:1) |
| » Tables | Home | Away | First round | Second round |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester City | 15 | 10 | 2 | 3 | 23:9 | 14 | 32 |
| 2 |
|
Charlton Athletic | 15 | 10 | 2 | 3 | 29:17 | 12 | 32 |
| 3 |
|
Fulham FC | 15 | 7 | 7 | 1 | 17:8 | 9 | 28 |
| 4 |
|
Huddersfield Town | 15 | 7 | 4 | 4 | 28:19 | 9 | 25 |
| 5 |
|
Ipswich Town | 15 | 7 | 3 | 5 | 29:22 | 7 | 24 |
| 6 |
|
Queens Park Rangers | 15 | 6 | 6 | 3 | 24:18 | 6 | 24 |
| 7 |
|
Birmingham City | 15 | 6 | 5 | 4 | 24:17 | 7 | 23 |
| 8 |
|
Barnsley FC | 15 | 7 | 2 | 6 | 29:27 | 2 | 23 |
| 9 |
|
Stockport County | 15 | 6 | 5 | 4 | 19:21 | -2 | 23 |
| 10 |
|
Blackburn Rovers | 15 | 5 | 6 | 4 | 20:16 | 4 | 21 |
| 11 |
|
Wolverhampton Wanderers | 15 | 5 | 6 | 4 | 16:17 | -1 | 21 |
| 12 |
|
Norwich City | 15 | 5 | 5 | 5 | 16:16 | 0 | 20 |
| 13 |
|
Grimsby Town | 15 | 5 | 5 | 5 | 16:19 | -3 | 20 |
| 14 |
|
Nottingham Forest | 15 | 4 | 7 | 4 | 20:16 | 4 | 19 |
| 15 |
|
West Bromwich Albion | 15 | 3 | 9 | 3 | 13:13 | 0 | 18 |
| 16 |
|
Bolton Wanderers | 15 | 4 | 5 | 6 | 21:21 | 0 | 17 |
| 17 |
|
Portsmouth FC | 15 | 4 | 4 | 7 | 18:25 | -7 | 16 |
| 18 |
|
Crewe Alexandra | 15 | 4 | 4 | 7 | 17:24 | -7 | 16 |
| 19 |
|
Sheffield United | 15 | 4 | 4 | 7 | 19:27 | -8 | 16 |
| 20 |
|
Crystal Palace | 15 | 3 | 6 | 6 | 21:27 | -6 | 15 |
| 21 |
|
Tranmere Rovers | 15 | 3 | 4 | 8 | 18:27 | -9 | 13 |
| 22 |
|
Swindon Town | 15 | 3 | 4 | 8 | 12:23 | -11 | 13 |
| 23 |
|
Walsall FC | 15 | 3 | 4 | 8 | 12:25 | -13 | 13 |
| 24 |
|
Port Vale FC | 15 | 3 | 3 | 9 | 17:24 | -7 | 12 |
| Promotion | |
| Relegation |
