| 2. Round | 06/10/2020 | Weymouth FC | - | Woking FC | 0:1 | ||||
| 3. Round | 10/10/2020 | Weymouth FC | - | Sutton United | 0:1 | ||||
| 4. Round | 13/10/2020 | Barnet FC | - | Weymouth FC | 1:0 | ||||
| 5. Round | 17/10/2020 | Weymouth FC | - | King's Lynn | 2:1 |  |
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| 6. Round | 27/10/2020 | Bromley FC | - | Weymouth FC | 3:2 | ||||
| 7. Round | 31/10/2020 | Stockport County | - | Weymouth FC | 1:2 | |
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| 13. Round | 05/12/2020 | Weymouth FC | - | Halifax Town | 1:5 | ||||
| 14. Round | 08/12/2020 | Weymouth FC | - | Dagenham & Redbridge | 2:3 | ||||
| 15. Round | 12/12/2020 | Wealdstone FC | - | Weymouth FC | 2:1 | ||||
| 8. Round | 15/12/2020 | Weymouth FC | - | Wrexham AFC | 2:3 | ||||
| 27. Round | 23/02/2021 | Yeovil Town | - | Weymouth FC | 3:1 | ||||
| 36. Round | 05/04/2021 | Halifax Town | - | Weymouth FC | 3:2 | ||||
| 43. Round | 08/05/2021 | Sutton United | - | Weymouth FC | 2:0 | ||||
| 10. Round | 11/05/2021 | Solihull Moors | - | Weymouth FC | 2:1 | ||||
| 24. Round | 18/05/2021 | Weymouth FC | - | Boreham Wood | 1:3 | ||||
| 45. Round | 22/05/2021 | Notts County | - | Weymouth FC | 3:0 | ||||
| 40. Round | 29/05/2021 | Hartlepool United | - | Weymouth FC | 4:0 |
England