| Tuesday 10th August 1999 | |||
| First Round 1st Leg | |||
| Birmingham City | 3-0 | Exeter City | |
| Blackpool | 2-1 | Tranmere Rovers | |
| Bournemouth | 2-0 | Barnet | |
| Bury | 1-0 | Notts County | |
| Cambridge United | 2-2 | Bristol City | |
| Cardiff City | 1-2 | Queens Park Rangers | |
| Carlisle United | 0-0 | Grimsby Town | |
| Chester City | 2-1 | Port Vale | |
| Colchester United | 2-2 | Crystal Palace | |
| Darlington | 1-1 | Bolton Wanderers | |
| Halifax Town | 0-0 | West Bromwich Albion | |
| Hartlepool United | 3-3 | Crewe Alexandra | |
| Lincoln City | 2-4 | Barnsley | |
| Luton Town | 0-2 | Bristol Rovers | |
| Macclesfield Town | 1-1 | Stoke City | |
| Northampton Town | 1-2 | Fulham | |
| Norwich City | 2-0 | Cheltenham Town | |
| Preston North End | 1-0 | Wrexham | |
| Rochdale | 1-2 | Chesterfield | |
| Rotherham United | 0-1 | Hull City | |
| Scunthorpe United | 0-2 | Huddersfield Town | |
| Sheffield United | 3-0 | Shrewsbury Town | |
| Southend United | 0-2 | Oxford United | |
| Stockport County | 2-0 | Oldham Athletic | |
| Swindon Town | 0-1 | Leyton Orient | |
| Walsall | 4-1 | Plymouth Argyle | |
| Wycombe Wanderers | 0-1 | Wolverhampton Wndrs | |
| York City | 0-1 | Wigan Athletic | |
» English League Cup 1999-2000 : Results
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