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| 1st(1st leg) | AFC Bournemouth | - | Barnet FC | 2:0 (1:0) | ||
| 2nd (2nd leg) | Barnet FC | - | AFC Bournemouth | 3:2 (2:2) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: AFC Bournemouth | ||||
| 1st(1st leg) | Birmingham City | - | Exeter City | 3:0 (2:0) | ||
| 2nd (2nd leg) | Exeter City | - | Birmingham City | 1:2 (0:1) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Birmingham City | ||||
| 1st(1st leg) | Blackpool FC | - | Tranmere Rovers | 2:1 (1:1) | ||
| 2nd (2nd leg) | Tranmere Rovers | - | Blackpool FC | 3:1 (2:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Tranmere Rovers | ||||
| 1st(1st leg) | Bury FC | - | Notts County | 1:0 (0:0) | ||
| 2nd (2nd leg) | Notts County | - | Bury FC | 2:0 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Notts County | ||||
| 1st(1st leg) | Cambridge United | - | Bristol City | 2:2 (0:0) | ||
| 2nd (2nd leg) | Bristol City | - | Cambridge United | 2:1 (2:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Bristol City | ||||
| 1st(1st leg) | Cardiff City | - | Queens Park Rangers | 1:2 (0:1) | ||
| 2nd (2nd leg) | Queens Park Rangers | - | Cardiff City | 2:3 (0:1, 0:1, 1:2) pso | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 25/08/1999 | Winner: Cardiff City | ||||
| 1st(1st leg) | Carlisle United | - | Grimsby Town | 0:0 (0:0) | ||
| 2nd (2nd leg) | Grimsby Town | - | Carlisle United | 6:0 (3:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Grimsby Town | ||||
| 1st(1st leg) | Chester City | - | Port Vale FC | 2:1 (1:1) | ||
| 2nd (2nd leg) | Port Vale FC | - | Chester City | 4:4 (2:2) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Chester City | ||||
| 1st(1st leg) | Colchester United | - | Crystal Palace | 2:2 (1:0) | ||
| 2nd (2nd leg) | Crystal Palace | - | Colchester United | 3:1 (2:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Crystal Palace | ||||
| 1st(1st leg) | Darlington FC | - | Bolton Wanderers | 1:1 (1:0) | ||
| 2nd (2nd leg) | Bolton Wanderers | - | Darlington FC | 5:3 (2:2) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Bolton Wanderers | ||||
| 1st(1st leg) | Halifax Town | - | West Bromwich Albion | 0:0 (0:0) | ||
| 2nd (2nd leg) | West Bromwich Albion | - | Halifax Town | 5:1 (4:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: West Bromwich Albion | ||||
| 1st(1st leg) | Hartlepool United | - | Crewe Alexandra | 3:3 (1:1) | ||
| 2nd (2nd leg) | Crewe Alexandra | - | Hartlepool United | 1:0 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Crewe Alexandra | ||||
| 1st(1st leg) | Lincoln City | - | Barnsley FC | 2:4 (1:3) | ||
| 2nd (2nd leg) | Barnsley FC | - | Lincoln City | 2:2 (0:1) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Barnsley FC | ||||
| 1st(1st leg) | Luton Town | - | Bristol Rovers | 0:2 (0:1) | ||
| 2nd (2nd leg) | Bristol Rovers | - | Luton Town | 2:2 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 25/08/1999 | Winner: Bristol Rovers | ||||
| 1st(1st leg) | Macclesfield Town | - | Stoke City | 1:1 (0:1) | ||
| 2nd (2nd leg) | Stoke City | - | Macclesfield Town | 3:0 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 25/08/1999 | Winner: Stoke City | ||||
| 1st(1st leg) | Northampton Town | - | Fulham FC | 1:2 (0:0) | ||
| 2nd (2nd leg) | Fulham FC | - | Northampton Town | 3:1 (3:1) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Fulham FC | ||||
| 1st(1st leg) | Norwich City | - | Cheltenham Town | 2:0 (2:0) | ||
| 2nd (2nd leg) | Cheltenham Town | - | Norwich City | 2:1 (0:0, 2:0) aet | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Norwich City | ||||
| 1st(1st leg) | Preston North End | - | Wrexham AFC | 1:0 (1:0) | ||
| 2nd (2nd leg) | Wrexham AFC | - | Preston North End | 0:2 (0:1) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Preston North End | ||||
| 1st(1st leg) | Rochdale AFC | - | Chesterfield FC | 1:2 (1:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): | |||||
| 1st(1st leg) | Rotherham United | - | Hull City | 0:1 (0:1) | ||
| 2nd (2nd leg) | Hull City | - | Rotherham United | 2:0 (1:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Hull City | ||||
| 1st(1st leg) | Scunthorpe United | - | Huddersfield Town | 0:2 (0:1) | ||
| 2nd (2nd leg) | Huddersfield Town | - | Scunthorpe United | 0:0 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Huddersfield Town | ||||
| 1st(1st leg) | Sheffield United | - | Shrewsbury Town | 3:0 (0:0) | ||
| 2nd (2nd leg) | Shrewsbury Town | - | Sheffield United | 0:3 (0:2) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Sheffield United | ||||
| 1st(1st leg) | Southend United | - | Oxford United | 0:2 (0:0) | ||
| 2nd (2nd leg) | Oxford United | - | Southend United | 1:0 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Oxford United | ||||
| 1st(1st leg) | Stockport County | - | Oldham Athletic | 2:0 (0:0) | ||
| 2nd (2nd leg) | Oldham Athletic | - | Stockport County | 1:1 (0:1) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Stockport County | ||||
| 1st(1st leg) | Swindon Town | - | Leyton Orient | 0:1 (0:0) | ||
| 2nd (2nd leg) | Leyton Orient | - | Swindon Town | 1:1 (0:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Leyton Orient | ||||
| 1st(1st leg) | Walsall FC | - | Plymouth Argyle | 4:1 (1:1) | ||
| 2nd (2nd leg) | Plymouth Argyle | - | Walsall FC | 1:4 (1:3) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Walsall FC | ||||
| 1st(1st leg) | Wycombe Wanderers | - | Wolverhampton Wanderers | 0:1 (0:0) | ||
| 2nd (2nd leg) | Wolverhampton Wanderers | - | Wycombe Wanderers | 2:4 (0:2) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Wycombe Wanderers | ||||
| 1st(1st leg) | York City | - | Wigan Athletic | 0:1 (0:0) | ||
| 2nd (2nd leg) | Wigan Athletic | - | York City | 2:1 (1:0) | ||
| 1st(1st leg): 10/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Wigan Athletic | ||||
| 1st(1st leg) | Brentford FC | - | Ipswich Town | 0:2 (0:0) | ||
| 2nd (2nd leg) | Ipswich Town | - | Brentford FC | 2:0 (1:0) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Ipswich Town | ||||
| 1st(1st leg) | Brighton & Hove Albion | - | Gillingham FC | 0:2 (0:1) | ||
| 2nd (2nd leg) | Gillingham FC | - | Brighton & Hove Albion | 2:0 (2:0) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Gillingham FC | ||||
| 1st(1st leg) | Manchester City | - | Burnley FC | 5:0 (1:0) | ||
| 2nd (2nd leg) | Burnley FC | - | Manchester City | 0:1 (0:0) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Manchester City | ||||
| 1st(1st leg) | Nottingham Forest | - | Mansfield Town | 3:0 (1:0) | ||
| 2nd (2nd leg) | Mansfield Town | - | Nottingham Forest | 1:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Nottingham Forest | ||||
| 1st(1st leg) | Reading FC | - | Peterborough United | 0:0 (0:0) | ||
| 2nd (2nd leg) | Peterborough United | - | Reading FC | 1:2 (1:1) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Reading FC | ||||
| 1st(1st leg) | Swansea City | - | Millwall FC | 2:0 (1:0) | ||
| 2nd (2nd leg) | Millwall FC | - | Swansea City | 1:1 (1:0) | ||
| 1st(1st leg): 11/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Swansea City | ||||
| 1st(1st leg) | Torquay United | - | Portsmouth FC | 0:0 (0:0) | ||
| 2nd (2nd leg) | Portsmouth FC | - | Torquay United | 3:0 (2:0) | ||
| 1st(1st leg): 17/08/1999 | 2nd (2nd leg): 24/08/1999 | Winner: Portsmouth FC | ||||
