İngiltere| 23.11.1999 | ENG L2 | Cheltenham | 2-0 | Plymouth Argyle |  |
| 16.11.1999 | ENG L2 | Swansea City | 0-0 | Cheltenham |  |
| 12.11.1999 | ENG L2 | Northampton | 3-2 | Cheltenham |  |
| 06.11.1999 | ENG L2 | Cheltenham | 3-1 | Carlisle United | |
| 02.11.1999 | ENG L2 | Halifax | 1-1 | Cheltenham | |
| 23.10.1999 | ENG L2 | Cheltenham | 0-0 | Brighton | |
| 19.10.1999 | ENG L2 | Chester FC | 2-1 | Cheltenham | |
| 16.10.1999 | ENG L2 | Darlington | 1-0 | Cheltenham | |
| 09.10.1999 | ENG L2 | Cheltenham | 2-1 | Southend United | |
| 02.10.1999 | ENG L2 | Cheltenham | 0-2 | Rotherham | |
| 25.09.1999 | ENG L2 | Brighton | 1-0 | Cheltenham | |
| 18.09.1999 | ENG L2 | Peterborough | 1-0 | Cheltenham | |
| 12.09.1999 | ENG L2 | Cheltenham | 0-1 | Shrewsbury | |
| 30.08.1999 | ENG L2 | Cheltenham | 1-2 | Barnet | |
| 28.08.1999 | ENG L2 | Hartlepool United | 0-1 | Cheltenham | |
| 21.08.1999 | ENG L2 | Cheltenham | 1-0 | Hull City | |
| 14.08.1999 | ENG L2 | Mansfield | 0-1 | Cheltenham | |
| 07.08.1999 | ENG L2 | Cheltenham | 0-2 | Rochdale | |
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