| 2023-11-29 19:45:2929th November 2023 |   Weymouth Under 23’s v AFC Stoneham U23’s | 19:45:297:45 pm | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-11-22 19:45:2322nd November 2023 |  Fareham Town U23’s v Weymouth Under 23’s | 19:45:237:45 pm | Hampshire Combination & Development Football League | |
| 2023-11-16 19:45:0716th November 2023 |  Weymouth Under 23’s v Laverstock & Ford U23’s | 19:45:077:45 pm | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-11-07 19:45:477th November 2023 |  Havant & Waterlooville U23’s v Weymouth Under 23’s | 1 - 3 | Hampshire Combination & Development Football League | |
| 2023-11-01 19:45:411st November 2023 |  Weymouth Under 23’s v Millbrook U23’s | 19:45:41Postponed | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-10-25 19:45:4125th October 2023 | Weymouth Under 23’s v Fareham Town U23’s | 19:45:41Postponed | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-10-18 19:45:3718th October 2023 | Weymouth Under 23’s v Havant & Waterlooville U23’s | 19:45:37Postponed | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-10-05 19:45:135th October 2023 | Millbrook U23’s v Weymouth Under 23’s | 0 - 3 | Hampshire Combination & Development Football League | |
| 2023-09-26 19:45:0126th September 2023 | AFC Stoneham U23’s v Weymouth Under 23’s | 0 - 10 | Hampshire Combination & Development Football League | |
| 2023-09-21 19:45:4421st September 2023 |  Gillingham Town U23’s v Weymouth Under 23’s | 0 - 5 | Hampshire Combination & Development Football League | |
| 2023-09-14 19:45:3714th September 2023 | Laverstock & Ford Reserves v Weymouth Under 23’s | 2 - 0 | John Stimpson Memorial Shield | |
| 2023-09-07 19:45:177th September 2023 | Laverstock & Ford U23’s v Weymouth Under 23’s | 2 - 6 | Hampshire Combination & Development Football League | |
| 2023-08-30 19:45:3030th August 2023 |  Dorchester Town U23’s v Weymouth Under 23’s | 3 - 0 | Hampshire Combination & Development Football League | Avenue Stadium |
| 2023-08-23 19:45:3323rd August 2023 |  Weymouth Under 23’s v Winchester City U23’s | 3 - 0 | Hampshire Combination & Development Football League | Bob Lucas Stadium |
| 2023-08-05 15:00:545th August 2023 |  Chertsey Town v Weymouth Under 23’s | 2 - 0 | Friendly - U23's | |
| 2023-07-29 15:00:4729th July 2023 |  Bovey Tracey AFC v Weymouth Under 23’s | 2 - 3 | Friendly - U23's | |
| 2023-07-25 19:00:3925th July 2023 |  Blandford United v Weymouth Under 23’s | 4 - 2 | Friendly - U23's | |
| 2023-07-18 19:45:1818th July 2023 |  Hamworthy United Reserves v Weymouth Under 23’s | 2 - 2 | Friendly - U23's | The County Ground |
| 2023-07-14 19:30:2214th July 2023 |  Hamworthy Recreation v Weymouth Under 23’s | 3 - 1 | Friendly - U23's | Magna Road |
| 2023-07-12 19:15:3312th July 2023 |  Weymouth Under 23’s v Bournemouth Poppies | 1 - 5 | Friendly - U23's | Redlands Community Sports Hub |
| 2023-07-03 19:00:473rd July 2023 |  Balti Sports v Weymouth Under 23’s | 0 - 6 | Friendly - U23's | Redlands Community Sports Hub |
