| 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 |
| 2019-08-03 16:00:00August 3, 2019 | Moruga F.C. vs RSSR F.C. | 1 - 0 | 2019 | Grand Chemin Rec. Grd. | Match Day 4 |
| 2019-08-11 16:00:00August 11, 2019 | RSSR F.C. vs Police F.C. | 0 - 1 | 2019 | Dibe Rec. Ground, Long Circular | Match Day 5 |
| 2019-08-18 18:00:00August 18, 2019 | Bethel United vs RSSR F.C. | 3 - 1 | 2019 | Mt. Gomery Rec. Grd. | Match Day 6 |
| 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 |
| 2019-09-18 19:00:00September 18, 2019 | RSSR F.C. vs San Fernando Giants | 0 - 3 | 2019 | Curepe Rec. Grd., Knowles St. | Match Day 8 |
