Cup of Jamaica season 27
Cup of Jamaica
| Tournament | Season | Champion |
|---|---|---|
 Cup | 84 | Negril Beach |
| Cup | 83 | Negril Beach |
| Cup | 82 | Negril Beach |
| Cup | 81 | Negril Beach |
| Cup | 80 | Negril Beach |
| Cup | 79 | Negril Beach |
| Cup | 78 | Negril Beach |
| Cup | 77 | Negril Beach |
| Cup | 76 | Negril Beach |
| Cup | 75 | Negril Beach |
| Cup | 74 | FC Portmore #2 |
| Cup | 73 | Negril Beach |
| Cup | 72 | Negril Beach |
| Cup | 71 | Negril Beach |
| Cup | 70 | Negril Beach |
| Cup | 69 | Negril Beach |
| Cup | 68 | Negril Beach |
| Cup | 67 | Negril Beach |
| Cup | 66 | FC Kingston #4 |
| Cup | 65 | FC Kingston #4 |
| Cup | 64 | Negril Beach |
| Cup | 63 | Negril Beach |
| Cup | 62 | Negril Beach |
| Cup | 61 | FC Kingston #4 |
| Cup | 60 | Negril Beach |
The cup winner qualifies for North American League season 28 (Group stage)
If the cup winner qualified for the champions league then the cup ticket goes to the best team in the league that doesn't qualify for the champions league.