| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1929/30 | Fourth Round Proper - 1 | 25/01/1930 | Middlesbrough | 1 - 1 | Charlton Athletic | [33] | ||||
| 2 | FA Cup 1929/30 | Fourth Round Proper - 2 | 29/01/1930 | Charlton Athletic | 1 - 1 | Middlesbrough | [33] | ||||
| 3 | FA Cup 1929/30 | Fourth Round Proper - 2 | 03/02/1930 | Middlesbrough | 1 - 0 | Charlton Athletic | [33] | ||||
| 4 | FA Cup 1956/57 | Third Round Proper - 1 | 05/01/1957 | Middlesbrough | 1 - 1 | Charlton Athletic | [33] | ||||
| 5 | FA Cup 1956/57 | Third Round Proper - 2 | 10/01/1957 | Charlton Athletic | 2 - 3 | Middlesbrough | [33] | ||||
| 6 | FA Cup 1964/65 | Fourth Round Proper - 1 | 30/01/1965 | Charlton Athletic | 1 - 1 | Middlesbrough | [33] | ||||
| 7 | FA Cup 1964/65 | Fourth Round Proper - 2 | 01/02/1965 | Middlesbrough | 2 - 1 | Charlton Athletic | [33] | ||||
| 8 | FA Cup 2005/06 | Sixth Round Proper - 1 | 23/03/2006 | Charlton Athletic | 0 - 0 | Middlesbrough | [33] | ||||
| 9 | FA Cup 2005/06 | Sixth Round Proper - 2 | 12/04/2006 | Middlesbrough | 4 - 2 | Charlton Athletic | [33] |
