| Sr.# | Match # | Match Date | Ground | Toronto Woodlands Score | Opposition & Score | Result | Points |
| 1 | 35 | Saturday, May 11, 2019 | Batsman Park - North | 183 for 6 in 23.0 overs | Punjab XI A 182 for 7 in 23.0 overs |
Toronto Woodlands won by 4 wickets |
10 |
| 2 | 56 | Sunday, May 12, 2019 | Batsman Park - South | 132 all out in 20.0 overs | Punjab XI A 208 for 5 in 25.0 overs |
Punjab XI A won by 76 runs |
0 |
| 3 | 50 | Saturday, May 18, 2019 | Batsman Park - North | 151 all out in 23.5 overs | York 155 for 7 in 23.4 overs |
York won by 3 wickets |
0 |
| 4 | 606 | Sunday, May 19, 2019 | Teramoto Park | 163 for 5 in 24.0 overs | Youngstars I 162 all out in 24.5 overs |
Toronto Woodlands won by 5 wickets |
10 |
| 5 | 612 | Sunday, May 26, 2019 | Teramoto Park | 129 for 9 in 20.0 overs | PHAT Sixers 150 for 5 in 20.0 overs |
PHAT Sixers won by 21 runs |
0 |
| 6 | 588 | Saturday, Jun 01, 2019 | Powerade-Lower (South) (Right) | 149 all out in 25.0 overs | Brampton Royals 185 for 5 in 25.0 overs |
Brampton Royals won by 36 runs |
0 |
| 7 | 57 | Sunday, Jun 09, 2019 | Teramoto Park | 148 all out in 24.0 overs | Goldie Warriors 152 for 2 in 22.0 overs (Target: 149 runs) |
Goldie Warriors won by 8 wickets |
0 |
| 8 | 40 | Sunday, Jun 16, 2019 | Batsman Park - North | 211 for 8 in 26.0 overs | Goldie Warriors 137 all out in 22.5 overs (Target: 212 runs) |
Toronto Woodlands won by 75 runs |
10 |
| 9 | 60 | Sunday, Jul 07, 2019 | Andrew McCandless Park | 170 for 6 in 25.0 overs | BoomBoom 171 for 2 in 22.4 overs |
BoomBoom won by 8 wickets |
0 |
| 10 | 45 | Saturday, Jul 13, 2019 | Batsman Park - North | 196 for 8 in 25.0 overs | Jazba 197 for 2 in 21.3 overs |
Jazba won by 8 wickets |
0 |
| 11 | 594 | Sunday, Jul 21, 2019 | Andrew McCandless Park | 218 for 5 in 25.0 overs | Indian Royals 204 for 8 in 25.0 overs |
Toronto Woodlands won by 14 runs |
10 |
| 12 | 58 | Sunday, Aug 11, 2019 | Andrew McCandless Park | 163 for 8 in 24.0 overs | Jazba 164 for 3 in 19.3 overs |
Jazba won by 7 wickets |
0 |
| 13 | 600 | Saturday, Aug 17, 2019 | Batsman Park - South | Ahmadiyya |
Match abandoned | 5 | |
| 14 | 59 | Saturday, Aug 31, 2019 | Batsman Park - North | 151 all out in 25.0 overs | York 154 for 2 in 10.4 overs |
York won by 8 wickets |
0 |
| 15 | 582 | Saturday, Sep 07, 2019 | Powerade-Upper (North) (Center) | 150 for 1 in 18.4 overs | Blazing Star 146 for 8 in 23.0 overs |
Toronto Woodlands won by 9 wickets |
10 |
| 16 | 55 | Saturday, Sep 14, 2019 | Batsman Park - North | 228 for 7 in 25.0 overs | BoomBoom 184 all out in 23.2 overs |
Toronto Woodlands won by 44 runs |
10 |