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This article needs to be updated. Please help update this article to reflect recent events or newly available information. (December 2021)
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| Tournament details | |
|---|---|
| Country | Saint Kitts and Nevis |
← 2017–18
2019–20 →
| |
This tournament started on 26 February 2019 with preliminary round.
Played on 26 and 28 February 2019[1]
| Home team | Away team | Result |
|---|---|---|
| United Old Road Jets | Newton Ground Ballers | 3–0 Awarded |
| Security Forces United FC | Davis Construction Lodge Patriots FC | 3–2 |
| Mantab United | Rivers of Living Water | 3–0 |
| KFC Trinity/Challengers United FC | Caribbean Cable Bath United | 3–0 Awarded |
| Hardtimes United | Molineux FC | 6–0 |
Played on 19 and 21 March 2019[2]
| Home team | Away team | Result |
|---|---|---|
| St. Paul's United | Sandy Point FC | 2–1 |
| Conaree FC | Mantab United | 1–0 |
| Cayon Rockets | Security Forces United FC | 3–0 |
| Saddlers United | United Old Road Jets | 4–2 |
| Garden Hotspurs | KFC Trinity/Challengers United FC | 2–1 |
| Newtown United | Hardtimes United | 3–0 |
| Village Superstars | Trafalgar Southstars | 2–0 |
| Dieppe Bay Eagles FC | St. Peters Strikers | 2–7 |
Played on 29, 30 and 31 March 2019[3]
| Home team | Away team | Result |
|---|---|---|
| Cayon Rockets | St. Peters Strikers | 2–2 (5–4 p) |
| Conaree FC | St. Paul's United | 2–2 (6–5 p) |
| Village Superstars | Saddlers United | 4–1 |
| Newtown United | Garden Hotspurs | 4–0 |
In bold, players that continue active in the competition.
| Rank | Player | Club | Goals |
|---|---|---|---|
| 1 |  Niquan Phipps
|
Saddlers United | 3 |
| 2 | Dionis Stephens
|
St. Peters Strikers | 3 |
| 3 | Denroy Matthew
|
Saddlers United | 2 |
| 4 | Orlando Mitchum
|
Newtown United | 2 |
| 5 | Chevaun Walwyn
|
Hardtimes United | 2 |
| 6 | Vinceroy Nelson
|
Cayon Rockets | 2 |
| 7 | Sylvester Alexander
|
Mantab United | 2 |
| 8 | Kareem Harris
|
St. Peters Strikers | 2 |
| 9 | Joseph Wilkes
|
Village Superstars | 2 |
| 10 | Errol O'Loughlin
|
Conaree FC | 2 |
