| 2018-07-28 10:00:59July 28, 2018 | AFC Stoneham v Wimborne Town FC SWC | 0 - 3 | SW18 Friendlies | 2018 | | Recap |
| 2018-08-18 12:30:13August 18, 2018 | Wimborne Town FC U18 SWC v Sholing FC | 2 - 0 | SW18 Friendlies | 2018 | Blandford School | Recap |
| 2018-09-01 11:00:18September 1, 2018 | Wimborne SWCYL v Team BTC | 2 - 0 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-09-07 19:45:09September 7, 2018 | Wimborne SWCL v Champion Sports | 4 - 2 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-09-20 19:45:09September 20, 2018 | FA YOUTH CUP | 4 - 2 | FA Youth | 2018 | N/A | Recap |
| 2018-09-22 11:00:18September 22, 2018 | Wimborne SWCYL v Salisbury | 5 - 0 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-09-29 11:00:09September 29, 2018 | Torquay AC v Wimborne SWCL | 1 - 2 | Under 18s South West Counties Youth League | 2018 | Seale Hayne | Recap |
| 2018-10-06 11:00:18October 6, 2018 | Wimborne SWCYL v Bath City League Cup | 0 - 3 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-10-11 19:45:41October 11, 2018 | Wimborne Town FC U18 SWCYL-v-Totton & Eling Youth U18 | 3 - 1 | u18s floodlit cup | 2018 | Cuthbury | Recap |
| 2018-10-13 10:30:09October 13, 2018 | Bristol AC v Wimborne SWCL | 0 - 2 | Under 18s South West Counties Youth League | 2018 | Wise Campus | Recap |
| 2018-10-20 11:00:18October 20, 2018 | Wimborne SWCYL v New College Swindon | 8 - 2 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-10-27 11:00:18October 27, 2018 | Wimborne SWCYL v Cirencester League Cup | 2 - 5 | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-11-10 11:00:09November 10, 2018 | Bath City v Wimborne SWCL | 1 - 3 | Under 18s South West Counties Youth League | 2018 | Twerton Park | Recap |
| 2018-11-17 11:00:09November 17, 2018 | Team BTC v Wimborne SWCL League Cup | 3 - 5 | Under 18s South West Counties Youth League | 2018 | Bridgwater & Taunton College | Recap |
| 2018-11-24 11:00:18November 24, 2018 | Wimborne SWCYL v Cirencester | 11:00:18Postponed | Under 18s South West Counties Youth League | 2018 | Blandford School | Recap |
| 2018-12-01 11:00:18December 1, 2018 | New College Swindon v Wimborne SWCYL | 3 - 5 | Under 18s South West Counties Youth League | 2018 | Supermarine Sports & Social Club | Recap |
| 2018-12-08 11:00:18December 8, 2018 | Salisbury v Wimborne SWCYL League Cup | 2 - 9 | Under 18s South West Counties Youth League | 2018 | BULFORD 3G PITCH | Recap |
| 2018-12-15 10:30:09December 15, 2018 | Wimborne SWCL v Champion Sports | 10:30:09Postponed | Under 18s South West Counties Youth League | 2018 | REDLANDS SPORTS HUB | Recap |
| 2018-12-17 19:45:15December 17, 2018 | Camberley Town (U18) Ryman v Wimborne Town FC U18 | 19:45:15Postponed | u18s floodlit cupUnder 18s South West Counties Youth League | 2018 | | Recap |
| 2019-01-05 11:00:18January 5, 2019 | New College Swindon v Wimborne SWCYL League Cup | 5 - 4 | Under 18s South West Counties Youth League | 20182019 | Supermarine Sports & Social Club | Recap |
| 2019-01-07 19:45:06January 7, 2019 | Camberley FC u18 V Wimborne SWC u18 | 0 - 0 | u18s floodlit cup | 20182019 | | Recap |
| 2019-01-12 11:00:09January 12, 2019 | Wimborne SWCL v Torquay AC | 11:00:09Postponed | Under 18s South West Counties Youth League | 20182019 | Blandford School | Recap |
| 2019-01-19 10:30:18January 19, 2019 | Cirencester v Wimborne SWCYL | 1 - 5 | Under 18s South West Counties Youth League | 20182019 | The Corinium Stadium | Recap |
| 2019-01-26 11:00:09January 26, 2019 | Wimborne SWCL v Bristol AC league Cup | 11:00:09Postponed | Under 18s South West Counties Youth League | 20182019 | Blandford School | Recap |
| 2019-01-28 19:45:04January 28, 2019 | Camberley FC vs WIMBORNE SW U18S | 1 - 1 | u18s floodlit cupUnder 18s South West Counties Youth League | | | Recap |
