| 2023-05-09 19:00:00May 9, 2023 | Hamilton Thunder vs Waterdown Bulldogs | 4 - 0 | |
| 2023-05-16 21:00:00May 16, 2023 | Waterdown Bulldogs vs Rockton Blazers | 2 - 2 | |
| 2023-05-23 19:00:00May 23, 2023 | BCFC vs Waterdown Bulldogs | 1 - 2 | |
| 2023-06-15 21:00:00June 15, 2023 | Dundas Assault vs Waterdown Bulldogs | 0 - 0 | |
| 2023-06-20 21:00:00June 20, 2023 | Waterdown Bulldogs vs Hamilton Thunder | 0 - 1 | |
| 2023-06-27 19:00:00June 27, 2023 | Wentworth FC vs Waterdown Bulldogs | 0 - 1 | |
| 2023-07-04 21:00:00July 4, 2023 | BCFC vs Waterdown Bulldogs | 6 - 1 | |
| 2023-07-06 19:00:00July 6, 2023 | Rockton Blazers vs Waterdown Bulldogs | 2 - 2 | |
| 2023-07-13 21:00:00July 13, 2023 | Waterdown Bulldogs vs Dundas Assault | 2 - 1 | |
| 2023-07-18 21:00:00July 18, 2023 | Waterdown Bulldogs vs Ancaster FC | 4 - 4 | |
| 2023-07-25 21:00:00July 25, 2023 | Waterdown Bulldogs vs Wentworth FC | 0 - 3 | |
| 2023-08-01 21:00:00August 1, 2023 | Waterdown Bulldogs vs Hamilton Thunder | 1 - 3 | |
| 2023-08-10 21:00:00August 10, 2023 | Rockton Blazers vs Waterdown Bulldogs | 0 - 4 | |
| 2023-08-29 19:00:00August 29, 2023 | Ancaster FC vs Waterdown Bulldogs | 5 - 3 | |
| 2023-09-05 19:00:00September 5, 2023 | Waterdown Bulldogs vs Ancaster FC | 2 - 5 | |
| 2023-09-07 21:00:00September 7, 2023 | Waterdown Bulldogs vs BCFC | 5 - 1 | |
| 2023-09-12 21:00:08September 12, 2023 | QF#1 - BCFC vs Waterdown Bulldogs | 2 - 3 | |
| 2023-09-19 21:00:22September 19, 2023 | SF#1 - Ancaster FC vs Waterdown Bulldogs | 7 - 3 | |
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