| 2019-07-13 17:00:00July 13, 2019 | Police F.C. vs Petit Valley/Diego Martin Utd | 2 - 1 | 2019 | Police Academy, St. James | Match Day 1 |
| 2019-07-21 16:00:00July 21, 2019 | Petit Valley/Diego Martin Utd. vs UTT | 2 - 2 | 2019 | Diego Martin Sport Complex | Match Day 2 |
| 2019-07-28 16:00:00July 28, 2019 | Petit Valley/Diego Martin Utd. vs San Fernando Giants | 0 - 1 | 2019 | St. Anthony's College Grd. | Match Day 3 |
| 2019-08-04 16:00:00August 4, 2019 | Petit Valley/Diego Martin Utd. vs Bethel United | 1 - 0 | 2019 | St. Anthony's College Grd. | Match Day 4 |
| 2019-08-11 19:00:00August 11, 2019 | Deportivo P.F. vs Petit Valley/Diego Martin Utd. | 3 - 0 | 2019 | Mahaica Oval, Rec. 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 |
| 2019-08-25 16:00:00August 25, 2019 | Petit Valley/Diego Martin Utd. vs Erin F.C. | 0 - 1 | 2019 | St. Anthony's College Grd. | Match Day 7 |
| 2019-09-01 16:00:00September 1, 2019 | Marabella Family Crisis Centre vs Petit Valley/Diego Martin Utd. | 1 - 0 | 2019 | Marabella Recreation Grd. | Match Day 8 |
| 2019-09-07 18:30:00September 7, 2019 | Club Sando Uprising Youths vs Petit Valley/Diego Martin Utd. | 6 - 2 | 2019 | Guapo Rec. Grd. | Match Day 9 |
| 2019-09-15 16:00:00September 15, 2019 | RSSR F.C. vs Petit Valley/Diego Martin Utd. | 3 - 2 | 2019 | Curepe Rec. Grd., Knowles St. | Match Day 10 |
| 2019-09-29 16:00:00September 29, 2019 | Petit Valley/Diego Martin Utd. vs Moruga F.C. | 3 - 2 | 2019 | St. Anthony's College Grd. | Match Day 11 |
