Results from the 2014–15 Cayman Islands FA Cup
Schedule
First round
- Sunset 0-2 Cayman Brac
- Future 0-1 Academy
[Mar 8]
- George Town 3-1 East End
[Mar 10]
- Scholars 1-2 Bodden Town
[Mar 11]
- Elite 11-2 Savannah Tigers
- Latinos 4-6 Cayman Athletic
- Roma United bye North Side
Quarter-finals
| 11 April 2015 | Cayman Athletic | 4–0 | Cayman Brac | George Town |
| Report | Stadium: Truman Bodden Sports Complex |
| 12 April 2015 | North Side | 1–3 | Elite SC | North Side |
| Report | Stadium: North Side Town Field |
| 12 April 2015 | Future | 0–5 | Bodden Town | West Bay |
| Report | Stadium: West Bay Town Field |
| 12 April 2015 | Roma United | 1–3 | George Town | George Town |
| Report | Stadium: Truman Bodden Sports Complex |
Semi-finals
| 26 April 2015 | Bodden Town | 0–2 | Cayman Athletic | Bodden Town |
| Report | Stadium: Bodden Town Stadium |
| 26 April 2015 | George Town | 2–3 | Elite | George Town |
| Report | Stadium: Truman Bodden Sports Complex |
Final
| 31 May 2015 | Cayman Athletic | 3–2 | Elite | George Town |
| Report | Stadium: Truman Bodden Sports Complex |