| Leeds United FC v Chelsea FC 10/10/1955 | View match | |
| Chelsea FC v Tottenham Hotspur FC 15/10/1955 | £11.00 | |
| Brentford FC v Chelsea FC 18/10/1955 | £35.99 | |
| Preston North End FC v Chelsea FC 22/10/1955 | View match | |
| Chelsea FC v Burnley FC 29/10/1955 | £8.50 | |
| Birmingham City FC v Chelsea FC 05/11/1955 | View match | |
| Millwall FC v Chelsea FC 07/11/1955 | View match | |
| Chelsea FC v West Bromwich Albion FC 12/11/1955 | View match | |
| Manchester United FC v Chelsea FC 19/11/1955 | View match | |
| Chelsea FC v Sheffield United FC 26/11/1955 | View match | |
| Everton FC v Chelsea FC 03/12/1955 | View match | |
| Chelsea FC v Newcastle United FC 10/12/1955 | View match |