| 2019-07-14 15:30:00July 14, 2019 | Cunupia F.C. vs Defence Force F.C. | 0 - 2 | 2019 | Larry Gomes Stadium | Match Day 1 |
| 2019-07-28 16:00:00July 28, 2019 | Club Sando F.C. vs Cunupia F.C. | 0 - 2 | 2019 | MRS, Training Field | Match Day 3 |
| 2019-08-04 16:00:00August 4, 2019 | San Juan Jabloteh vs Cunupia F.C. | 2 - 1 | 2019 | San Juan North Secondary School | Match Day 4 |
| 2019-08-11 18:00:00August 11, 2019 | Guaya United F.C. vs Cunupia F.C. | 1 - 2 | 2019 | Guaya Recreation Grd. | Match Day 5 |
| 2019-08-18 16:00:00August 18, 2019 | QPCC vs Cunupia F.C. | 1 - 1 | 2019 | St. Mary's College Grd. | Match Day 6 |
| 2019-08-24 18:00:00August 24, 2019 | Terminix La Horquetta Rangers F.C. vs Cunupia F.C. | 4 - 1 | 2019 | Phase 2 La Horquetta Rec. Grd. | Match Day 7 |
| 2019-09-14 15:30:00September 14, 2019 | Cunupia F.C. vs Caledonia AIA | 3 - 0 | 2019 | Larry Gomes Stadium | Match Day 10 |
| 2019-09-29 19:15:00September 29, 2019 | Cunupia F.C. vs Police F.C | 1 - 2 | 2019 | Diego Martin Sport Complex | Match Day 8 |
