| Arsenal FC v Nottingham Forest FC 15/11/1958 | £5.00 | |
| Arsenal FC v Blackpool FC 29/11/1958 | £4.50 | |
| Bury FC v Arsenal FC 10/01/1959 | £15.00 | |
| Arsenal FC v Everton FC 17/01/1959 | £5.50 | |
| Manchester City FC v Arsenal FC 07/02/1959 | £9.00 | |
| Arsenal FC v Sheffield United FC 14/02/1959 | £4.50 | |
| Arsenal FC v Manchester United FC 28/02/1959 | £4.50 | |
| Arsenal FC v Blackburn Rovers FC 14/03/1959 | £5.00 | |
| West Ham United FC v Arsenal FC 06/04/1959 | £17.50 | |
| Arsenal FC v Chelsea FC 11/04/1959 | £4.50 | |
| Arsenal FC v Sheffield Wednesday FC 22/08/1959 | £7.50 | |
| Arsenal FC v Nottingham Forest FC 01/09/1959 | £8.50 |