| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1958/59 | First Round Proper - 1 | 15/11/1958 | Colchester United | 2 - 0 | Bath City | [33] | ||||
| 2 | FA Cup 1958/59 | Second Round Proper - 1 | 06/12/1958 | Colchester United | 1 - 1 | Yeovil | [33] | ||||
| 3 | FA Cup 1958/59 | Second Round Proper - 2 | 11/12/1958 | Yeovil | 1 - 7 | Colchester United | [33] | ||||
| 4 | FA Cup 1958/59 | Third Round Proper - 1 | 10/01/1959 | Colchester United | 2 - 0 | Chesterfield | [33] | ||||
| 5 | FA Cup 1958/59 | Fourth Round Proper - 1 | 24/01/1959 | Colchester United | 2 - 2 | Arsenal | [33] | ||||
| 6 | FA Cup 1958/59 | Fourth Round Proper - 2 | 28/01/1959 | Arsenal | 4 - 0 | Colchester United | [33] |
