1. Round | 21/08/2021 | Halifax Town | - | Maidenhead United | 1:2 | ||||
2. Round | 28/08/2021 | Maidenhead United | - | Dover Athletic | 2:0 | ||||
3. Round | 30/08/2021 | Weymouth FC | - | Maidenhead United | 3:1 | ||||
4. Round | 04/09/2021 | Maidenhead United | - | Torquay United | 3:4 | ||||
6. Round | 14/09/2021 | Maidenhead United | - | Stockport County | 0:2 | ||||
16. Round | 20/11/2021 | Boreham Wood | - | Maidenhead United | 4:0 | ||||
17. Round | 07/12/2021 | Southend United | - | Maidenhead United | 1:1 | ||||
20. Round | 11/12/2021 | Maidenhead United | - | Solihull Moors | 0:4 |