Max no-draw streak
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7
non-draws in a row
05 May 1999 → 24 Oct 1999
Matches in this run
| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 05 May 1999 | Cuba | 4–1 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 07 May 1999 | Bermuda | 4–1 | Cayman Islands | H | ITL · CFU Caribbean Cup qualification |
| 09 May 1999 | Cayman Islands | 4–1 | Bahamas | H | ITL · CFU Caribbean Cup qualification |
| 09 Sep 1999 | Bermuda | 3–1 | Cayman Islands | H | ITL · Friendly |
| 11 Sep 1999 | Bermuda | 1–0 | Cayman Islands | H | ITL · Friendly |
| 22 Sep 1999 | Cayman Islands | 4–0 | Bahamas | H | ITL · Friendly |
| 24 Oct 1999 | Cayman Islands | 1–4 | Jamaica | A | ITL · Friendly |