| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1929/30 | First Round Proper - 1 | 30/11/1929 | Southport | 0 - 0 | Chesterfield | [33] | ||||
| 2 | FA Cup 1929/30 | First Round Proper - 2 | 04/12/1929 | Chesterfield | 3 - 2 | Southport | [33] | ||||
| 3 | FA Cup 1929/30 | Second Round Proper - 1 | 14/12/1929 | Chesterfield | 2 - 0 | Port Vale | [33] | ||||
| 4 | FA Cup 1929/30 | Third Round Proper - 1 | 11/01/1930 | Chesterfield | 1 - 1 | Middlesbrough | [33] | ||||
| 5 | FA Cup 1929/30 | Third Round Proper - 2 | 15/01/1930 | Middlesbrough | 4 - 3 | Chesterfield | [33] |
