| 2020-09-01 19:45:541st September 2020 |   AFC Totton vs Weymouth | Friendly | N/A | Recap |
| 2020-09-05 15:00:055th September 2020 |  Weymouth 3-1 Havant & Waterlooville | Friendly | N/A | Recap |
| 2020-09-08 19:45:558th September 2020 |  Dorchester Town 1-3 Weymouth | Friendly | N/A | Recap |
| 2020-09-12 15:00:3412th September 2020 |  Weymouth 4-0 Poole Town | Friendly | N/A | Recap |
| 2020-09-15 19:00:5215th September 2020 |  Weymouth 1-1 Exeter City | Friendly | N/A | Recap |
| 2020-09-19 15:00:5819th September 2020 |  Slough Town vs Weymouth | Friendly | N/A | Recap |
| 2020-09-26 15:00:1526th September 2020 |  Weymouth vs Ebbsfleet United | Friendly | N/A | Recap |
| 2020-10-03 15:00:123rd October 2020 |  Altrincham 0-0 Weymouth | National League | N/A | Recap |
| 2020-10-06 19:45:166th October 2020 |  Weymouth 0-1 Woking | National League | N/A | Recap |
| 2020-10-10 15:00:1510th October 2020 |  Weymouth 0-1 Sutton United | National League | N/A | Recap |
| 2020-10-13 19:45:0013th October 2020 |  Barnet 1-0 Weymouth | National League | N/A | Recap |
| 2020-10-17 15:00:0017th October 2020 |  Weymouth 2-1 King's Lynn Town | National League | N/A | Recap |
| 2020-10-24 15:00:0024th October 2020 |  Weymouth vs Oxford City | FA Cup | N/A | Recap |
| 2020-10-27 19:45:0027th October 2020 |  Bromley vs Weymouth | National League | N/A | Recap |
| 2020-10-31 15:00:0031st October 2020 |  Stockport County vs Weymouth | National League | N/A | Recap |
| 2020-11-28 15:00:0028th November 2020 |  Weymouth 1-2 Chesterfield | National League | N/A | Recap |
| 2020-12-05 17:20:005th December 2020 |  Weymouth 1-5 Halifax Town | National League | N/A | Recap |
| 2020-12-08 19:45:008th December 2020 |  Weymouth 2-3 Dagenham & Redbridge | National League | N/A | Recap |
| 2020-12-12 15:00:0012th December 2020 |  Wealdstone 2-1 Weymouth | National League | N/A | Recap |
| 2020-12-15 19:45:5915th December 2020 |  Weymouth 2-3 Wrexham | National League | N/A | Recap |
| 2020-12-19 15:00:1519th December 2020 |  Weymouth 3-2 Maidenhead United | FA Trophy | N/A | Recap |
| 2020-12-26 15:00:0026th December 2020 |  Eastleigh 0-0 Weymouth | National League | N/A | Recap |
| 2020-12-28 15:00:0028th December 2020 |  Weymouth 3-4 Torquay United | National League | N/A | Recap |
| 2021-01-02 15:00:002nd January 2021 | Weymouth 1-1 Eastleigh | National League | N/A | Recap |
| 2021-01-05 19:45:395th January 2021 |  Weymouth 0-3 Yeovil Town | National League | N/A | Recap |
| 2021-01-16 15:00:0716th January 2021 |  Weymouth 0-1 Darlington | FA Trophy | N/A | Recap |
| 2021-01-23 15:00:0023rd January 2021 |  Weymouth 1-0 Hartlepool United | National League | N/A | Recap |
| 2021-01-26 19:45:0026th January 2021 |  Aldershot Town 0-2 Weymouth | National League | N/A | Recap |
| 2021-01-30 15:00:0030th January 2021 |  Weymouth vs Notts County | National League | N/A | Recap |
| 2021-02-02 19:45:262nd February 2021 |  Boreham Wood 1-0 Weymouth | National League | N/A | Recap |
| 2021-02-06 15:00:006th February 2021 | Weymouth 2-1 Bromley | National League | N/A | Recap |
| 2021-02-20 15:00:0020th February 2021 |  Weymouth 0-0 Solihull Moors | National League | N/A | Recap |
| 2021-02-23 19:45:0023rd February 2021 | Yeovil Town 3-1 Weymouth | National League | N/A | Recap |
| 2021-02-27 15:00:0027th February 2021 | King’s Lynn Town 2-2 Weymouth | National League | N/A | Recap |
| 2021-03-06 15:00:006th March 2021 | Weymouth 1-0 Stockport County | National League | N/A | Recap |
| 2021-03-13 15:00:0013th March 2021 | Wrexham 2-0 Weymouth | National League | N/A | Recap |
| 2021-03-16 19:45:0016th March 2021 | Dagenham & Redbridge vs Weymouth | National League | N/A | Recap |
| 2021-03-20 15:00:0020th March 2021 | Weymouth 4-0 Wealdstone | National League | N/A | Recap |
| 2021-03-27 15:00:0027th March 2021 | Chesterfield 1-0 Weymouth | National League | N/A | Recap |
| 2021-04-02 15:00:002nd April 2021 | Weymouth 2-1 Maidenhead United | National League | N/A | Recap |
| 2021-04-05 15:00:005th April 2021 | Halifax Town 3-2 Weymouth | National League | N/A | Recap |
| 2021-04-10 15:00:0010th April 2021 | Torquay United vs Weymouth | National League | N/A | Recap |
| 2021-04-13 19:45:0013th April 2021 | Weymouth vs Aldershot Town | National League | N/A | Recap |
| 2021-04-27 19:45:5227th April 2021 | Maidenhead United vs Weymouth | National League | N/A | Recap |
| 2021-05-01 15:00:001st May 2021 | Woking vs Weymouth | National League | N/A | Recap |
| 2021-05-03 15:00:003rd May 2021 | Weymouth vs Barnet | National League | N/A | Recap |
| 2021-05-08 15:00:008th May 2021 | Sutton United vs Weymouth | National League | N/A | Recap |
| 2021-05-11 19:00:4111th May 2021 | Solihull Moors vs Weymouth | National League | N/A | Recap |
| 2021-05-15 15:00:0015th May 2021 | Weymouth vs Altrincham | National League | N/A | Recap |
| 2021-05-18 19:45:0018th May 2021 | Weymouth vs Boreham Wood | National League | N/A | Recap |
| 2021-05-22 15:00:0022nd May 2021 | Notts County vs Weymouth | National League | N/A | Recap |
| 2021-05-29 12:30:0029th May 2021 | Hartlepool United vs Weymouth | National League | N/A | Recap |
