| 2023-05-18 21:00:00May 18, 2023 | Wentworth FC vs Hamilton Thunder | 1 - 2 | |
| 2023-05-25 21:00:00May 25, 2023 | Ancaster FC vs Wentworth FC | 5 - 1 | |
| 2023-05-30 21:00:00May 30, 2023 | Wentworth FC vs Dundas Assault | 2 - 0 | |
| 2023-06-13 19:00:00June 13, 2023 | BCFC vs Wentworth FC | 2 - 2 | |
| 2023-06-22 21:00:00June 22, 2023 | Wentworth FC vs Ancaster FC | 2 - 5 | |
| 2023-06-27 19:00:00June 27, 2023 | Wentworth FC vs Waterdown Bulldogs | 0 - 1 | |
| 2023-07-04 19:00:00July 4, 2023 | Hamilton Thunder vs Wentworth FC | 0 - 0 | |
| 2023-07-11 21:00:00July 11, 2023 | Wentworth FC vs BCFC | 5 - 1 | |
| 2023-07-17 19:00:00July 17, 2023 | Rockton Blazers vs Wentworth FC | 1 - 4 | |
| 2023-07-20 21:00:00July 20, 2023 | Dundas Assault vs Wentworth FC | 0 - 3 | |
| 2023-07-25 21:00:00July 25, 2023 | Waterdown Bulldogs vs Wentworth FC | 0 - 3 | |
| 2023-08-08 19:00:00August 8, 2023 | Hamilton Thunder vs Wentworth FC | 1 - 2 | |
| 2023-08-15 21:00:00August 15, 2023 | Wentworth FC vs Ancaster FC | 8 - 1 | |
| 2023-08-22 19:00:00August 22, 2023 | Dundas Assault vs Wentworth FC | 1 - 1 | |
| 2023-08-29 21:00:00August 29, 2023 | Wentworth FC vs Rockton Blazers | 5 - 3 | |
| 2023-09-05 21:00:00September 5, 2023 | Wentworth FC vs Rockton Blazers | 2 - 1 | |
| 2023-09-14 21:00:05September 14, 2023 | QF#2 - Wentworth FC vs Dundas Assault | 4 - 0 | |
| 2023-09-21 21:00:05September 21, 2023 | SF#2 - Hamilton Thunder vs Wentworth FC | 1 - 0 | |
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