| Sr.# | Match # | Match Date | Ground | Toronto Woodlands Score | Opposition & Score | Result | Points |
| 1 | 418 | Saturday, May 06, 2023 | Batsman Park - North | 206 for 9 in 37.2 overs | Redhawks 205 all out in 46.3 overs |
Toronto Woodlands won by 1 wickets |
11 |
| 2 | 9 | Saturday, May 20, 2023 | Andrew McCandless Park | 204 for 7 in 25.0 overs | Cardinal Sports Academy 146 all out in 23.0 overs (Target: 205 runs) |
Toronto Woodlands won by 58 runs |
11 |
| 3 | 21 | Sunday, May 28, 2023 | Batsman Park - North | 259 all out in 35.1 overs | B Pacers 136 all out in 28.0 overs |
Toronto Woodlands won by 123 runs |
11 |
| 4 | 23 | Sunday, Jun 04, 2023 | Batsman Park - South | 250 all out in 47.0 overs | Phoenix 202 all out in 41.0 overs |
Toronto Woodlands won by 48 runs |
10 |
| 5 | 419 | Saturday, Jun 10, 2023 | Andrew McCandless Park | 134 for 8 in 23.2 overs | Mississauga Leopards - 3FG Sports 128 all out in 32.0 overs |
Toronto Woodlands won by 2 wickets |
11 |
| 6 | 30 | Sunday, Jun 18, 2023 | Dixie-407 - C (North-West) | 230 all out in 45.0 overs | Yorkshire 199 all out in 41.0 overs |
Toronto Woodlands won by 31 runs |
10 |
| 7 | 416 | Sunday, Jun 25, 2023 | Batsman Park - South | 210 all out in 40.0 overs | Jhanvi 86 all out in 23.2 overs |
Toronto Woodlands won by 124 runs |
11 |
| 8 | 25 | Saturday, Jul 15, 2023 | Batsman Park - South | Yorkshire |
Match rained out | 5 | |
| 9 | 22 | Saturday, Jul 22, 2023 | Andrew McCandless Park | 231 all out in 47.4 overs | Cardinal Sports Academy 190 all out in 43.4 overs |
Toronto Woodlands won by 41 runs |
10 |
| 10 | 24 | Sunday, Jul 30, 2023 | Teramoto Park | 27 for 1 in 4.2 overs | The Fighters 26 all out in 18.0 overs |
Toronto Woodlands won by 9 wickets |
11 |
| 11 | 19 | Saturday, Aug 12, 2023 | Gore Meadows | 143 for 2 in 25.3 overs | The Fighters 140 all out in 30.0 overs |
Toronto Woodlands won by 8 wickets |
11 |
| 12 | 415 | Saturday, Aug 19, 2023 | Batsman Park - South | 128 all out in 31.0 overs | BTown Warriors 219 all out in 42.0 overs |
BTown Warriors won by 91 runs |
0 |
| 13 | 417 | Saturday, Sep 02, 2023 | Andrew McCandless Park | 156 all out in 27.3 overs | National 213 for 9 in 47.0 overs |
National won by 57 runs |
0 |
| 14 | 603 | Sunday, Sep 10, 2023 | Batsman Park - South | 200 for 6 in 32.1 overs | Phoenix 196 all out in 45.0 overs |
Toronto Woodlands won by 4 wickets |
11 |
| 15 | 4 | Sunday, Sep 17, 2023 | Batsman Park - South | 240 for 5 in 37.0 overs | B Pacers 127 for 8 in 20.0 overs (Target: 232 runs) |
Toronto Woodlands won by 104 runs |
11 |
| 16 | 420 | Sunday, Sep 24, 2023 | Courtneypark Ground (Mississauga) | 172 all out in 31.0 overs | Ontario Cricket Academy 149 all out in 38.0 overs |
Toronto Woodlands won by 23 runs |
10 |