| Datum | Tijd | Huis | Weg | Dag van de wedstrijd | Wedstrijd | ||||
|---|---|---|---|---|---|---|---|---|---|
| 2022-08-12 | Harlem United |  | 3-0 |  | Mahaut Soca | QF | |||
| 2021-02-06 | Harlem United | | 1-5 |  | Sagicor South East Utd | SF | |||
| 2021-01-27 | Harlem United | | 3-0 | | Mahaut Soca | QF | |||
| 2021-01-21 | Harlem United | | 2-1 |  | East Central FC | L16 | |||
| 2019-10-14 | 20:00 | Dominica |  | 0-4 |  | Nicaragua | Grp.D |
