| Millwall FC v York City FC 29/11/1958 | View match | |
| Worcester City v Millwall FC 06/12/1958 | View match | |
| Millwall FC v Port Vale FC 13/12/1958 | View match | |
| Millwall FC v Gillingham FC 20/12/1958 | View match | |
| Millwall FC v Chester City FC 25/12/1958 | View match | |
| Chester City FC v Millwall FC 27/12/1958 | View match | |
| Carlisle United FC v Millwall FC 03/01/1959 | View match | |
| Millwall FC v Northampton Town FC 10/01/1959 | View match | |
| Millwall FC v Barrow 17/01/1959 | View match | |
| Bradford Park Avenue v Millwall FC 24/01/1959 | View match | |
| Crystal Palace FC v Millwall FC 28/01/1959 | View match | |
| Oldham Athletic FC v Millwall FC 31/01/1959 | View match |