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| 27/08/1999 | 19:45 | Stockport County | - | Birmingham City | 2:0 (0:0) | |
| 19:45 | Crewe Alexandra | - | Grimsby Town | 1:1 (0:0) | ||
| 28/08/1999 | 15:00 | Barnsley FC | - | Portsmouth FC | 6:0 (1:0) | |
| 15:00 | Bolton Wanderers | - | Manchester City | 0:1 (0:1) | ||
| 15:00 | Fulham FC | - | Charlton Athletic | 2:1 (2:0) | ||
| 15:00 | Huddersfield Town | - | Crystal Palace | 7:1 (3:0) | ||
| 15:00 | Norwich City | - | Blackburn Rovers | 0:2 (0:1) | ||
| 15:00 | Nottingham Forest | - | Queens Park Rangers | 1:1 (1:0) | ||
| 15:00 | Port Vale FC | - | Tranmere Rovers | 1:0 (0:0) | ||
| 15:00 | Sheffield United | - | Ipswich Town | 2:2 (0:2) | ||
| 15:00 | Swindon Town | - | West Bromwich Albion | 1:2 (1:0) | ||
| 15:00 | Wolverhampton Wanderers | - | Walsall FC | 1:2 (1:2) |
| » Tables | Home | Away | First round | Second round |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Ipswich Town | 4 | 3 | 1 | 0 | 10:4 | 6 | 10 |
| 2 |
|
Charlton Athletic | 4 | 3 | 0 | 1 | 7:3 | 4 | 9 |
| 3 |
|
Stockport County | 4 | 3 | 0 | 1 | 5:3 | 2 | 9 |
| 4 |
|
West Bromwich Albion | 4 | 2 | 2 | 0 | 6:4 | 2 | 8 |
| 5 |
|
Manchester City | 4 | 2 | 1 | 1 | 7:1 | 6 | 7 |
| 6 |
|
Birmingham City | 4 | 2 | 1 | 1 | 7:6 | 1 | 7 |
| 7 |
|
Portsmouth FC | 4 | 2 | 1 | 1 | 5:7 | -2 | 7 |
| 8 |
|
Barnsley FC | 4 | 2 | 0 | 2 | 11:7 | 4 | 6 |
|
Huddersfield Town | 4 | 2 | 0 | 2 | 11:7 | 4 | 6 | |
| 10 |
|
Fulham FC | 4 | 1 | 3 | 0 | 5:4 | 1 | 6 |
| 11 |
|
Crewe Alexandra | 4 | 1 | 2 | 1 | 6:5 | 1 | 5 |
|
Queens Park Rangers | 4 | 1 | 2 | 1 | 6:5 | 1 | 5 | |
| 13 |
|
Wolverhampton Wanderers | 4 | 1 | 2 | 1 | 4:4 | 0 | 5 |
| 14 |
|
Nottingham Forest | 4 | 1 | 2 | 1 | 5:6 | -1 | 5 |
| 15 |
|
Walsall FC | 4 | 1 | 2 | 1 | 4:6 | -2 | 5 |
| 16 |
|
Blackburn Rovers | 4 | 1 | 1 | 2 | 5:5 | 0 | 4 |
| 17 |
|
Bolton Wanderers | 4 | 1 | 1 | 2 | 2:3 | -1 | 4 |
|
Tranmere Rovers | 4 | 1 | 1 | 2 | 2:3 | -1 | 4 | |
| 19 |
|
Port Vale FC | 4 | 1 | 1 | 2 | 4:6 | -2 | 4 |
| 20 |
|
Swindon Town | 4 | 1 | 1 | 2 | 4:7 | -3 | 4 |
| 21 |
|
Crystal Palace | 4 | 1 | 1 | 2 | 6:12 | -6 | 4 |
| 22 |
|
Grimsby Town | 4 | 0 | 2 | 2 | 3:5 | -2 | 2 |
| 23 |
|
Sheffield United | 4 | 0 | 2 | 2 | 3:11 | -8 | 2 |
| 24 |
|
Norwich City | 4 | 0 | 1 | 3 | 1:5 | -4 | 1 |
| Promotion | |
| Relegation |
