| 2019-07-21 16:00:00July 21, 2019 | San Juan Jabloteh vs Police F.C | 3 - 1 | 2019 | San Juan North Secondary School | 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 |
| 2019-08-04 16:00:00August 4, 2019 | San Juan Jabloteh vs Cunupia F.C. | 2 - 1 | 2019 | San Juan North Secondary School | Match Day 4 |
| 2019-08-18 16:00:00August 18, 2019 | San Juan Jabloteh vs Prison Service F.C. | 2 - 1 | 2019 | San Juan North Secondary School | Match Day 6 |
| 2019-09-14 16:00:00September 14, 2019 | San Juan Jabloteh vs Guaya United F.C. | 3 - 1 | 2019 | San Juan North Secondary School | Match Day 8 |
| 2019-09-19 16:00:00September 19, 2019 | QPCC vs San Juan Jabloteh | 0 - 3 | 2019 | Dibe Rec. Ground, Long Circular | Match Day 10 |
| 2019-09-27 18:00:00September 27, 2019 | Terminix La Horquetta Rangers F.C. vs San Juan Jabloteh | 5 - 0 | 2019 | Phase 2 La Horquetta Rec. Grd. | Match Day 1 |
