| West Ham United FC v Arsenal FC 06/04/1959 | £20.00 | |
| Arsenal FC v Sheffield Wednesday FC 22/08/1959 | £7.50 | |
| Arsenal FC v Nottingham Forest FC 01/09/1959 | £8.50 | |
| Arsenal FC v Tottenham Hotspur FC 05/09/1959 | £10.50 | |
| Arsenal FC v Manchester City FC 12/09/1959 | £5.00 | |
| Arsenal FC v Manchester City FC 12/09/1959 | £3.50 | |
| Blackburn Rovers FC v Arsenal FC 19/09/1959 | £4.50 | |
| Arsenal FC v Blackpool FC 26/09/1959 | £6.50 | |
| Arsenal FC v Blackpool FC 26/09/1959 | £6.00 | |
| Manchester United FC v Arsenal FC 10/10/1959 | £4.50 | |
| Arsenal FC v Preston North End FC 17/10/1959 | £10.50 | |
| Arsenal FC v Birmingham City FC 31/10/1959 | £4.50 |