| 2019-07-21 16:00:00July 21, 2019 | Caledonia AIA vs Club Sando F.C. | 0 - 1 | 2019 | MRS, Training Field #2 | Match Day 2 |
| 2019-07-28 16:00:00July 28, 2019 | San Juan Jabloteh vs Caledonia AIA | 1 - 2 | 2019 | San Juan North Secondary School | Match Day 3 |
| 2019-08-11 16:00:00August 11, 2019 | Caledonia AIA vs QPCC | 4 - 2 | 2019 | St. Mary's College Grd. | Match Day 5 |
| 2019-08-17 16:00:00August 17, 2019 | Police F.C. vs Caledonia AIA | 0 - 1 | 2019 | Larry Gomes Stadium | Match Day 6 |
| 2019-09-01 18:00:00September 1, 2019 | Guaya United F.C. vs Caledonia AIA | 1 - 2 | 2019 | Guaya Recreation Grd. | Match Day 11 |
| 2019-09-07 18:00:00September 7, 2019 | Terminix La Horquetta Rangers F.C. vs Caledonia AIA | 0 - 2 | 2019 | Phase 2 La Horquetta Rec. Grd. | Match Day 4 |
| 2019-09-14 15:30:00September 14, 2019 | Cunupia F.C. vs Caledonia AIA | 3 - 0 | 2019 | Larry Gomes Stadium | Match Day 10 |
