| 2022-08-11 19:59:1011/08/2022 |   Aspatria FC 8-3 Workington AFC Development | 8 - 3 | | Development Friendlies 22/23 | Memorial Park |
| 2022-08-03 19:30:0103/08/2022 |  Kirkby Stephen 0-3 Workington AFC Development | 0 - 3 | | Development Friendlies 22/23 | Parrots Park |
| 2022-07-27 19:30:2127/07/2022 |  Penrith Reserves 3-6 Workington AFC Development | 3 - 6 | | Development Friendlies 22/23 | Frenchfield Park |
| 2022-07-20 19:30:4420/07/2022 |  Whitehaven 8-1 Workington AFC Development | 8 - 1 | | Development Friendlies 22/23 | County Ground |
| 2022-07-13 19:15:1313/07/2022 |  Queen of the South Youth 1-3 Workington AFC Development | 1 - 3 | | Development Friendlies 22/23 | Palmerston Park |
| 2022-07-06 19:00:0906/07/2022 |  Windscale 1-1 Workington AFC Development | 1 - 1 | | Development Friendlies 22/23 | |
| 2022-05-09 18:45:1709/05/2022 | Workington AFC Development 1-0 Aspatria FC (AET) | 1 - 0 | | Whitehaven Cup 2021/22 | Borough Park |
| 2022-04-23 14:00:2323/04/2022 |  Workington AFC Development vs Gosforth | 2 - 1 | | Whitehaven Cup 2021/22 | St Benedict's School |
| 2022-04-13 18:30:0213/04/2022 |  Workington Athletic 3-6 Workington Development | 3 - 6 | County League Premier 21/22 | County League Premier 2021/22 | Lakes College |
| 2022-04-09 14:00:1709/04/2022 |  Northbank 2-1 Workington AFC Development | 2 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Sheepmount, Carlisle |
| 2022-04-02 14:00:2302/04/2022 | Workington AFC Development 2-2 Aspatria FC | 2 - 2 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2022-03-26 14:00:3626/03/2022 |  Pirelli 5-1 Workington AFC Development | 5 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Pirelli FC |
| 2022-03-12 14:00:3912/03/2022 |  Workington AFC Development 7-3 Mirehouse | 7 - 3 | | Whitehaven Cup 2021/22 | St Benedict's School |
| 2022-03-05 14:00:3005/03/2022 | Workington AFC Development 3-1 Pirelli | 3 - 1 | | Whitehaven Cup 2021/22 | St Benedict's School |
| 2022-02-19 14:00:0119/02/2022 |  Wigton Harriers 1-1 Workington AFC Development | 1 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Barton Laws |
| 2022-02-12 14:00:4912/02/2022 | Workington AFC Development 3-1 Northbank | 3 - 1 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2022-01-29 14:00:0929/01/2022 |  Maryport Athletic 0-1 Workington AFC Development | 0 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Maryport ARLFC |
| 2022-01-22 14:00:3122/01/2022 |  Workington AFC Development 3-1 Cockermouth AFC | 3 - 1 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2022-01-15 13:30:5815/01/2022 |  Workington AFC Development 3-6 Whitehaven Miners Social (AET, 3-3 at 90 mins) | 3 - 6 | | Benevolent Cup 21/22 | St Benedict's School |
| 2021-12-11 14:00:2011/12/2021 | Gosforth 5-3 Workington AFC Development | 5 - 3 | County League Premier 21/22 | County League Premier 2021/22 | |
| 2021-12-04 14:00:0304/12/2021 | Workington AFC Development 0-4 Pirelli | 0 - 4 | | Conway Cup 21/22 | St Benedict's School |
| 2021-11-06 14:00:1306/11/2021 |  Workington AFC Development 10-0 Cleator Moor Celtic Reserves | 10 - 0 | | Conway Cup 21/22 | St Benedict's School |
| 2021-10-23 14:00:2823/10/2021 | Cockermouth FC 2-1 Workington AFC Development | 2 - 1 | County League Premier 21/22 | County League Premier 2021/22 | |
| 2021-10-16 14:00:1116/10/2021 |  Workington AFC Development 5-2 Carlisle City Development | 5 - 2 | | Conway Cup 21/22 | St Benedict's School |
| 2021-10-02 14:00:4602/10/2021 | Carlisle City Dev 3-2 Workington AFC Development | 3 - 2 | County League Premier 21/22 | County League Premier 2021/22 | Gilford Park |
| 2021-09-25 14:00:0225/09/2021 | Workington AFC Development 5-5 Workington Athletic | 5 - 5 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2021-09-18 14:00:1018/09/2021 | Workington AFC Development 1-1 Maryport Athletic | 1 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Borough Park |
| 2021-09-11 14:00:5911/09/2021 | Wigton Harriers 0-6 Workington AFC Development | 0 - 6 | County League Premier 21/22 | County League Premier 2021/22 | Barton Laws |
| 2021-09-04 14:00:2304/09/2021 | Workington AFC Development 2-2 Pirelli | 2 - 2 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2021-08-21 14:00:1621/08/2021 | Workington AFC Development 6-3 Gosforth AFC | 6 - 3 | County League Premier 21/22 | County League Premier 2021/22 | St Benedict's School |
| 2021-08-18 19:00:0818/08/2021 | Aspatria FC 4-1 Workington AFC Development | 4 - 1 | County League Premier 21/22 | County League Premier 2021/22 | Memorial Park |
| 2021-08-14 14:00:2414/08/2021 | Workington AFC Development 4-5 Carlisle City Dev | 4 - 5 | County League Premier 21/22 | County League Premier 2021/22 | Borough Park |
| 2021-08-06 19:00:1206/08/2021 |  Ulverston 2-2 Workington AFC Development | 2 - 2 | | Development Friendlies 21/22 | GSK Sports Complex |
| 2021-08-04 19:00:2704/08/2021 |  Bootle AFC 0-6 Workington AFC Development | 0 - 6 | | Development Friendlies 21/22 | Mill Holme |
| 2021-07-28 19:45:2428/07/2021 |  Holker Old Boys 8-1 Workington AFC Development | 8 - 1 | | Development Friendlies 21/22 | Handmark Engineering Stadium |
| 2021-07-24 14:00:4424/07/2021 | Workington AFC Development 3-0 Maryport Athletic | 3 - 0 | | Development Friendlies 21/22 | Borough Park |
| 2021-07-17 14:00:2617/07/2021 | Windscale 1-1 Workington AFC Development | 1 - 1 | | Development Friendlies 21/22 | |
| 2021-05-15 14:00:4715/05/2021 | Maryport Athletic 1-2 Workington AFC Development | 1 - 2 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | Maryport ARLFC |
| 2021-05-08 14:00:5608/05/2021 | Workington AFC Development 2-1 Cockermouth FC | 2 - 1 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | St Benedict's School |
| 2021-05-05 19:00:0605/05/2021 |  Morecambe Academy 8-1 Workington AFC Development | 8 - 1 | | Friendlies Development Team 2020/21 | Lancaster & Morecambe College |
| 2021-05-01 14:00:2701/05/2021 | Workington AFC Development 1-1 Maryport Athletic | 1 - 1 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | St Benedict's School |
| 2021-04-24 14:00:3524/04/2021 | Cleator Moor Celtic Reserves 4-4 Workington AFC Development | 4 - 4 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | Inglenorth Park |
| 2021-04-17 14:00:0217/04/2021 | Cockermouth FC 2-2 Workington AFC Development | 2 - 2 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | Grassmoor Sports Centre |
| 2021-04-13 18:30:5813/04/2021 |  Carlisle United Academy 3-5 Workington AFC Development | 3 - 5 | | | Caldew School |
| 2021-04-10 14:00:1710/04/2021 |  Workington AFC Development 5-3 Kirkoswald FC | 5 - 3 | | | Borough Park |
| 2021-04-06 18:30:3906/04/2021 | Workington AFC Development 1-4 Cleator Moor Celtic Reserves | 1 - 4 | Cumberland County League West Division 1 | County League West Division 1 (2020/21) | Borough Park |
| 2021-04-03 13:00:5903/04/2021 | Workington AFC Development 4-2 Aspatria FC | 4 - 2 | | Friendlies Development Team 2020/21 | Borough Park |
| 2020-12-19 14:00:3319/12/2020 | Workington AFC Development 5-3 Millom | 5 - 3 | | Friendlies Development Team 2020/21 | St Benedict's School |
| 2020-12-12 14:00:2712/12/2020 | Gosforth AFC 2-4 Workington AFC Development | 2 - 4 | | Friendlies Development Team 2020/21 | St Benedict's School |
| 2020-12-05 14:00:2305/12/2020 |  Crown Newlaithes vs Workington AFC Development | - | Cumberland County League Division 1 | County League Division 1 (2020/21) | Thursby Playing Fields |
| 2020-11-28 14:00:4028/11/2020 | Northbank vs Workington AFC Development | - | Cumberland County League Division 1 | County League Division 1 (2020/21) | Sheepmount, Carlisle |
| 2020-11-21 14:00:1221/11/2020 |  Workington AFC Development vs Moor Row | - | Cumberland County League Division 1 | County League Division 1 (2020/21) | Copeland Stadium |
| 2020-11-14 14:00:3114/11/2020 | Whitehaven Miners Social vs Workington AFC Development | - | Cumberland County League Division 1 | County League Division 1 (2020/21) | Recreation Ground, Whitehaven |
| 2020-11-07 14:00:1507/11/2020 | Workington AFC Development vs Whitehaven Miners Social | - | Cumberland County League Division 1 | County League Division 1 (2020/21) | Copeland Stadium |
| 2020-11-03 19:30:1303/11/2020 | Whitehaven AFC 3-4 Workington AFC Development | 3 - 4 | | Friendlies Development Team 2020/21 | Recreation Ground, Whitehaven |
| 2020-10-31 14:00:3931/10/2020 | Workington AFC Development 2-2 Northbank | 2 - 2 | | County League Division 1 (2020/21) | Copeland Stadium |
| 2020-10-24 14:00:2824/10/2020 |  Unisun Athletic 1-0 Workington AFC Development | 1 - 0 | | County League Division 1 (2020/21) | Melbourne Park |
| 2020-10-17 14:00:0617/10/2020 | Workington AFC Development 9-0 Mirehouse | 9 - 0 | | County League Division 1 (2020/21) | Copeland Stadium |
| 2020-10-10 14:00:3510/10/2020 | Pirelli 2-2 Workington AFC Development | 2 - 2 | | County League Division 1 (2020/21) | Pirelli FC |
| 2020-10-03 14:00:3003/10/2020 | Workington AFC Development 7-3 Windscale Reserves | 7 - 3 | | County League Division 1 (2020/21) | Copeland Stadium |
| 2020-09-26 12:00:3526/09/2020 | Workington AFC Development 1-4 Gosforth AFC | 1 - 4 | | Friendlies Development Team 2020/21 | Borough Park |
| 2020-09-19 14:00:3519/09/2020 | Aspatria FC 3 - 2 Workington AFC Development | 3 - 2 | | Friendlies Development Team 2020/21 | Memorial Park |
| 2020-09-16 19:00:2616/09/2020 | Workington AFC Development vs Windscale | 2 - 1 | | Friendlies Development Team 2020/21 | Borough Park |
| 2020-09-12 12:00:4912/09/2020 | Bootle AFC vs Workington AFC Development | 2 - 2 | | Friendlies Development Team 2020/21 | Mill Holme |
| 2020-08-26 18:45:5326/08/2020 | Kirkoswald FC vs Workington AFC Development | 4 - 3 | | Friendlies Development Team 2020/21 | The Old Showfield |
| 2020-08-15 14:00:3815/08/2020 | Cockermouth FC vs Workington AFC Development | - | | Friendlies Development Team 2020/21 | Grassmoor Sports Centre |
| 2020-08-14 18:30:3314/08/2020 | Carlisle United Youth vs Workington AFC Development | - | | Friendlies Development Team 2020/21 | Creighton RFC |
| 2020-08-10 19:00:4910/08/2020 | Workington Athletic vs Workington AFC Development | 2 - 5 | | Friendlies Development Team 2020/21 | Lakes College |
| 2020-08-08 12:00:5408/08/2020 |  Workington AFC Development vs Workington Juniors (Whites) | 0 - 1 | | Friendlies Development Team 2020/21 | Copeland Stadium |
