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| 1st(1st leg) | Barnsley FC | - | Stockport County | 1:1 (1:1) | ||
| 2nd (2nd leg) | Stockport County | - | Barnsley FC | 3:3 (2:0, 2:2) aet | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Barnsley FC | ||||
| 1st(1st leg) | Birmingham City | - | Bristol Rovers | 2:0 (0:0) | ||
| 2nd (2nd leg) | Bristol Rovers | - | Birmingham City | 0:1 (0:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Birmingham City | ||||
| 1st(1st leg) | Bradford City | - | Reading FC | 1:1 (1:0) | ||
| 2nd (2nd leg) | Reading FC | - | Bradford City | 2:2 (1:0, 1:1) aet | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Bradford City | ||||
| 1st(1st leg) | Crystal Palace | - | Leicester City | 3:3 (1:2) | ||
| 2nd (2nd leg) | Leicester City | - | Crystal Palace | 4:2 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Leicester City | ||||
| 1st(1st leg) | Cardiff City | - | Wimbledon FC | 1:1 (1:0) | ||
| 2nd (2nd leg) | Wimbledon FC | - | Cardiff City | 3:1 (0:1) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Wimbledon FC | ||||
| 1st(1st leg) | Charlton Athletic | - | AFC Bournemouth | 0:0 (0:0) | ||
| 2nd (2nd leg) | AFC Bournemouth | - | Charlton Athletic | 3:1 (0:0, 0:0, 0:0) pso | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: AFC Bournemouth | ||||
| 1st(1st leg) | Chester City | - | Aston Villa | 0:1 (0:0) | ||
| 2nd (2nd leg) | Aston Villa | - | Chester City | 5:0 (2:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Aston Villa | ||||
| 1st(1st leg) | Chesterfield FC | - | Middlesbrough FC | 0:0 (0:0) | ||
| 2nd (2nd leg) | Middlesbrough FC | - | Chesterfield FC | 2:1 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Middlesbrough FC | ||||
| 1st(1st leg) | Crewe Alexandra | - | Ipswich Town | 2:1 (0:1) | ||
| 2nd (2nd leg) | Ipswich Town | - | Crewe Alexandra | 1:1 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Crewe Alexandra | ||||
| 1st(1st leg) | Gillingham FC | - | Bolton Wanderers | 1:4 (0:2) | ||
| 2nd (2nd leg) | Bolton Wanderers | - | Gillingham FC | 2:0 (2:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Bolton Wanderers | ||||
| 1st(1st leg) | Grimsby Town | - | Leyton Orient | 4:1 (2:1) | ||
| 2nd (2nd leg) | Leyton Orient | - | Grimsby Town | 1:0 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Grimsby Town | ||||
| 1st(1st leg) | Huddersfield Town | - | Notts County | 2:1 (1:1) | ||
| 2nd (2nd leg) | Notts County | - | Huddersfield Town | 2:2 (2:2) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Huddersfield Town | ||||
| 1st(1st leg) | Hull City | - | Liverpool FC | 1:5 (0:2) | ||
| 2nd (2nd leg) | Liverpool FC | - | Hull City | 4:2 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Liverpool FC | ||||
| 1st(1st leg) | Norwich City | - | Fulham FC | 0:4 (0:1) | ||
| 2nd (2nd leg) | Fulham FC | - | Norwich City | 2:0 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Fulham FC | ||||
| 1st(1st leg) | Oxford United | - | Everton FC | 1:1 (1:1) | ||
| 2nd (2nd leg) | Everton FC | - | Oxford United | 0:1 (0:1) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Oxford United | ||||
| 1st(1st leg) | Portsmouth FC | - | Blackburn Rovers | 0:3 (0:0) | ||
| 2nd (2nd leg) | Blackburn Rovers | - | Portsmouth FC | 3:1 (0:1) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Blackburn Rovers | ||||
| 1st(1st leg) | Sheffield United | - | Preston North End | 2:0 (2:0) | ||
| 2nd (2nd leg) | Preston North End | - | Sheffield United | 3:0 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Preston North End | ||||
| 1st(1st leg) | Stoke City | - | Sheffield Wednesday | 0:0 (0:0) | ||
| 2nd (2nd leg) | Sheffield Wednesday | - | Stoke City | 3:1 (2:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Sheffield Wednesday | ||||
| 1st(1st leg) | Sunderland AFC | - | Walsall FC | 3:2 (1:2) | ||
| 2nd (2nd leg) | Walsall FC | - | Sunderland AFC | 0:5 (0:2) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Sunderland AFC | ||||
| 1st(1st leg) | Swansea City | - | Derby County | 0:0 (0:0) | ||
| 2nd (2nd leg) | Derby County | - | Swansea City | 3:1 (1:0) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Derby County | ||||
| 1st(1st leg) | Tranmere Rovers | - | Coventry City | 5:1 (0:1) | ||
| 2nd (2nd leg) | Coventry City | - | Tranmere Rovers | 3:1 (3:1) | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Tranmere Rovers | ||||
| 1st(1st leg) | Watford FC | - | Wigan Athletic | 2:0 (0:0) | ||
| 2nd (2nd leg) | Wigan Athletic | - | Watford FC | 3:1 (1:0, 3:1) aet | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Watford FC | ||||
| 1st(1st leg) | West Bromwich Albion | - | Wycombe Wanderers | 1:1 (0:0) | ||
| 2nd (2nd leg) | Wycombe Wanderers | - | West Bromwich Albion | 3:4 (1:2, 2:2) aet | ||
| 1st(1st leg): 14/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: West Bromwich Albion | ||||
| 1st(1st leg) | Manchester City | - | Southampton FC | 0:0 (0:0) | ||
| 2nd (2nd leg) | Southampton FC | - | Manchester City | 4:3 (2:1, 3:3) aet | ||
| 1st(1st leg): 15/09/1999 | 2nd (2nd leg): 21/09/1999 | Winner: Southampton FC | ||||
| 1st(1st leg) | Nottingham Forest | - | Bristol City | 2:1 (1:1) | ||
| 2nd (2nd leg) | Bristol City | - | Nottingham Forest | 0:0 (0:0) | ||
| 1st(1st leg): 15/09/1999 | 2nd (2nd leg): 22/09/1999 | Winner: Nottingham Forest | ||||
