| 2020-09-01 19:45:541st September 2020 | AFC Totton  | 0 - 1 |  Weymouth | Friendly | Recap |
| 2020-09-05 15:00:055th September 2020 | Weymouth | 3 - 1 |  Havant & Waterlooville | Friendly | Recap |
| 2020-09-08 19:45:558th September 2020 | Dorchester Town  | 1 - 3 | Weymouth | Friendly | Recap |
| 2020-09-12 15:00:3412th September 2020 | Weymouth | 4 - 0 |  Poole Town | Friendly | Recap |
| 2020-09-15 19:00:5215th September 2020 | Weymouth | 1 - 1 |  Exeter City | Friendly | Recap |
| 2020-09-19 15:00:5819th September 2020 | Slough Town  | 2 - 4 | Weymouth | Friendly | Recap |
| 2020-09-26 15:00:1526th September 2020 | Weymouth | 0 - 1 |  Ebbsfleet United | Friendly | Recap |
| 2020-10-03 15:00:123rd October 2020 | Altrincham  | 0 - 0 | Weymouth | National League | Recap |
| 2020-10-06 19:45:166th October 2020 | Weymouth | 0 - 1 |  Woking | National League | Recap |
| 2020-10-10 15:00:1510th October 2020 | Weymouth | 0 - 1 |  Sutton United | National League | Recap |
| 2020-10-13 19:45:0013th October 2020 | Barnet  | 1 - 0 | Weymouth | National League | Recap |
| 2020-10-17 15:00:0017th October 2020 | Weymouth | 2 - 1 |  King’s Lynn Town | National League | Recap |
| 2020-10-24 15:00:0024th October 2020 | Weymouth | 2 - 3 |  Oxford City | FA Cup | Recap |
| 2020-10-27 19:45:0027th October 2020 | Bromley  | 3 - 2 | Weymouth | National League | Recap |
| 2020-10-31 15:00:0031st October 2020 | Stockport County  | 1 - 2 | Weymouth | National League | Recap |
| 2020-11-28 15:00:0028th November 2020 | Weymouth | 1 - 2 |  Chesterfield | National League | Recap |
| 2020-12-05 17:20:005th December 2020 | Weymouth | 1 - 5 |  Halifax Town | National League | Recap |
| 2020-12-08 19:45:008th December 2020 | Weymouth | 2 - 3 |  Dagenham & Redbridge | National League | Recap |
| 2020-12-12 15:00:0012th December 2020 | Wealdstone  | 2 - 1 | Weymouth | National League | Recap |
| 2020-12-15 19:45:5915th December 2020 | Weymouth | 2 - 3 |  Wrexham | National League | Recap |
| 2020-12-19 15:00:1519th December 2020 | Weymouth | 3 - 2 |  Maidenhead United | FA Trophy | Recap |
| 2020-12-26 15:00:0026th December 2020 | Eastleigh  | 0 - 0 | Weymouth | National League | Recap |
| 2020-12-28 15:00:0028th December 2020 | Weymouth | 3 - 4 |  Torquay United | National League | Recap |
| 2021-01-02 15:00:002nd January 2021 | Weymouth | 1 - 1 | Eastleigh | National League | Recap |
| 2021-01-05 19:45:395th January 2021 | Weymouth | 0 - 3 |  Yeovil Town | National League | Recap |
| 2021-01-09 15:00:009th January 2021 | Dover Athletic  | P - P | Weymouth | National League | Recap |
| 2021-01-16 15:00:0716th January 2021 | Weymouth | 0 - 1 |  Darlington | FA Trophy | Recap |
| 2021-01-19 19:45:5519th January 2021 | Solihull Moors  | P - P | Weymouth | National League | Recap |
| 2021-01-23 15:00:0023rd January 2021 | Weymouth | - |  Hartlepool United | National League | Preview |
| 2021-01-26 19:45:0026th January 2021 | Aldershot Town  | - | Weymouth | National League | Preview |
| 2021-01-30 15:00:0030th January 2021 | Weymouth | - |  Notts County | National League | Preview |
| 2021-02-02 19:45:262nd February 2021 | Boreham Wood  | - | Weymouth | National League | Preview |
| 2021-02-09 19:45:009th February 2021 | Weymouth | - | Boreham Wood | National League | Preview |
| 2021-02-13 15:00:0013th February 2021 | Maidenhead United | - | Weymouth | National League | Preview |
| 2021-02-20 15:00:0020th February 2021 | Weymouth | - | Solihull Moors | National League | Preview |
| 2021-02-23 19:45:0023rd February 2021 | Yeovil Town | - | Weymouth | National League | Preview |
| 2021-02-27 15:00:0027th February 2021 | King’s Lynn Town | - | Weymouth | National League | Preview |
| 2021-03-06 15:00:006th March 2021 | Weymouth | - | Stockport County | National League | Preview |
| 2021-03-09 19:45:009th March 2021 | Weymouth | - | Bromley | National League | Preview |
| 2021-03-13 15:00:0013th March 2021 | Wrexham | - | Weymouth | National League | Preview |
| 2021-03-16 19:45:0016th March 2021 | Dagenham & Redbridge | - | Weymouth | National League | Preview |
| 2021-03-20 15:00:0020th March 2021 | Weymouth | - | Wealdstone | National League | Preview |
| 2021-03-27 15:00:0027th March 2021 | Chesterfield | - | Weymouth | National League | Preview |
| 2021-04-02 15:00:002nd April 2021 | Weymouth | - | Maidenhead United | National League | Preview |
| 2021-04-05 15:00:005th April 2021 | Halifax Town | - | Weymouth | National League | Preview |
| 2021-04-10 15:00:0010th April 2021 | Torquay United | - | Weymouth | National League | Preview |
| 2021-04-13 19:45:0013th April 2021 | Weymouth | - | Aldershot Town | National League | Preview |
| 2021-04-17 15:00:0017th April 2021 | Weymouth | - | Dover Athletic | National League | Preview |
| 2021-04-24 15:00:0024th April 2021 | Hartlepool United | - | Weymouth | National League | Preview |
| 2021-05-01 15:00:001st May 2021 | Woking | - | Weymouth | National League | Preview |
| 2021-05-03 15:00:003rd May 2021 | Weymouth | - | Barnet | National League | Preview |
| 2021-05-08 15:00:008th May 2021 | Sutton United | - | Weymouth | National League | Preview |
| 2021-05-15 15:00:0015th May 2021 | Weymouth | - | Altrincham | National League | Preview |
| 2021-05-22 15:00:0022nd May 2021 | Notts County | - | Weymouth | National League | Preview |
