| 2019-07-13 19:00:00July 13, 2019 | Deportivo P.F. vs Harlem Strikers | 7 - 0 | 2019 | Mahaica Oval, Point Fortin | Match Day 1 |
| 2019-07-21 17:30:00July 21, 2019 | Harlem Strikers vs Erin F.C. | 3 - 2 | 2019 | Frederick Settlement Grd. | Match Day 2 |
| 2019-07-28 16:00:00July 28, 2019 | RSSR F.C. vs Harlem Strikers | 0 - 0 | 2019 | Curepe Rec. Grd., Knowles St. | Match Day 3 |
| 2019-08-04 17:30:00August 4, 2019 | Harlem Strikers vs San Fernando Giants | 1 - 4 | 2019 | Frederick Settlement Grd. | Match Day 4 |
| 2019-08-11 17:30:00August 11, 2019 | Harlem Strikers vs Club Sando Uprising Youths | 0 - 4 | 2019 | Frederick Settlement Grd. | Match Day 5 |
| 2019-08-18 16:00:00August 18, 2019 | Petit Valley/Diego Martin Utd. vs Harlem Strikers | 2 - 1 | 2019 | St. Anthony's College Grd. | Match Day 6 |
| 2019-08-24 16:00:00August 24, 2019 | Moruga F.C. vs Harlem Strikers | 1 - 2 | 2019 | Grand Chemin Rec. Grd. | Match Day 7 |
| 2019-09-01 17:30:00September 1, 2019 | Harlem Strikers vs Police F.C. | 4 - 0 | 2019 | Frederick Settlement Grd. | Match Day 8 |
| 2019-09-07 17:30:00September 7, 2019 | Harlem Strikers vs UTT | 0 - 2 | 2019 | Frederick Settlement Grd. | Match Day 9 |
| 2019-09-14 17:30:00September 14, 2019 | Harlem Strikers vs Marabella Family Crisis Centre | 3 - 0 | 2019 | Frederick Settlement Grd. | Match Day 10 |
| 2019-09-28 15:30:00September 28, 2019 | Bethel United vs Harlem Strikers | 3 - 1 | 2019 | Mt. Gomery Rec. Grd. | Match Day 11 |
