| 11 Mar 2026 | SUR 92/7 v CAY 96/1Match 5 · T20I | CAY | DNB | 2/13 | 0 | Cayman Islands won by 9 wickets | George Town | ICC Men's T20 World Cup Sub Regional Americas Qualifier B 2025/26 |
| 9 Mar 2026 | MEX 94/9 v CAY 95/1Match 4 · T20I | CAY | DNB | 1/18 | 0 | Cayman Islands won by 9 wickets | George Town | ICC Men's T20 World Cup Sub Regional Americas Qualifier B 2025/26 |
| 8 Mar 2026 | ARG 98 v CAY 102/0Match 1 · T20I | CAY | DNB | 3/9 | 1 | Cayman Islands won by 10 wickets | George Town | ICC Men's T20 World Cup Sub Regional Americas Qualifier B 2025/26 |
| 26 Apr 2025 | CAY 122/8 v CAN 125/0Semi-final · T20I | CAY | 3* | 0/21 | 0 | Canada won by 10 wickets | George Town | North America T20 Cup 2025 |
| 24 Apr 2025 | CAY 175/2 v BAH 96/5Match 9 · T20I | CAY | DNB | 4/8 | 0 | Cayman Islands won by 79 runs | George Town | North America T20 Cup 2025 |
| 20 Apr 2025 | BER 137/5 v CAY 107/8Match 4 · T20I | CAY | 2* | 1/19 | 0 | Bermuda won by 30 runs | George Town | North America T20 Cup 2025 |
| 19 Apr 2025 | USA 186/6 v CAY 107/7Match 1 · T20I | CAY | DNB | 0/30 | 0 | United States of America won by 79 runs | George Town | North America T20 Cup 2025 |
| 16 Dec 2024 | BER 139/6 v CAY 126/9Match 33 · T20I | CAY | 0* | 2/20 | 0 | Bermuda won by 13 runs | Buenos Aires | ICC Men's T20 World Cup Sub Regional Americas Qualifier 2024/25 |
| 15 Dec 2024 | CAY 116 v ARG 94Match 30 · T20I | CAY | 0 | 1/22 | 0 | Cayman Islands won by 22 runs | Buenos Aires | ICC Men's T20 World Cup Sub Regional Americas Qualifier 2024/25 |
| 14 Dec 2024 | CAY 224/1 v BRA 65/9Match 25 · T20I | CAY | DNB | 1/2 | 0 | Cayman Islands won by 159 runs | Buenos Aires | ICC Men's T20 World Cup Sub Regional Americas Qualifier 2024/25 |
| 12 Dec 2024 | BAH 108/5 v CAY 109/0Match 23 · T20I | CAY | DNB | 0/15 | 0 | Cayman Islands won by 10 wickets | Buenos Aires | ICC Men's T20 World Cup Sub Regional Americas Qualifier 2024/25 |
| 10 Dec 2024 | CAY 142/8 v SUR 143/4Match 13 · T20I | CAY | DNB | 1/22 | 0 | Suriname won by 6 wickets | Buenos Aires | ICC Men's T20 World Cup Sub Regional Americas Qualifier 2024/25 |
| 4 Oct 2023 | CAN 196/5 v CAY 30Match 7 · T20I | CAY | 0 | 1/19 | 0 | Canada won by 166 runs | Hamilton | ICC Men's T20 World Cup Americas Region Final 2023/24 |
| 3 Oct 2023 | BER 176/6 v CAY 123/8Match 6 · T20I | CAY | DNB | 0/15 | 1 | Bermuda won by 53 runs | Hamilton | ICC Men's T20 World Cup Americas Region Final 2023/24 |
| 1 Oct 2023 | CAN 194/6 v CAY 86Match 4 · T20I | CAY | 4 | 1/38 | 1 | Canada won by 108 runs | Hamilton | ICC Men's T20 World Cup Americas Region Final 2023/24 |
| 30 Sept 2023 | PAN 85/8 v CAY 88/3Match 2 · T20I | CAY | DNB | 1/15 | 1 | Cayman Islands won by 7 wickets | Hamilton | ICC Men's T20 World Cup Americas Region Final 2023/24 |
| 4 Mar 2023 | ARG 125/7 v CAY 126/7Match 10 · T20I | CAY | 8 | 2/22 | 1 | Cayman Islands won by 3 wickets | Buenos Aires | ICC Men's T20 World Cup Americas Region Qualifier 2022/23 |
| 2 Mar 2023 | CAY 138/7 v PAN 126Match 7 · T20I | CAY | 11 | 3/24 | 1 | Cayman Islands won by 12 runs | Buenos Aires | ICC Men's T20 World Cup Americas Region Qualifier 2022/23 |
| 28 Feb 2023 | CAY 125 v BAH 94/8Match 5 · T20I | CAY | 4 | 2/22 | 1 | Cayman Islands won by 31 runs | Buenos Aires | ICC Men's T20 World Cup Americas Region Qualifier 2022/23 |
| 25 Feb 2023 | BER 173/3 v CAY 77/9Match 2 · T20I | CAY | 25 | 0/21 | 0 | Bermuda won by 96 runs | Buenos Aires | ICC Men's T20 World Cup Americas Region Qualifier 2022/23 |
| 17 Apr 2022 | CAY 180/6 v BAH 138/75th T20I · T20I | CAY | 2 | 2/18 | 0 | Cayman won by 42 runs | George Town | Bahamas in Cayman Islands 2022 |
| 14 Apr 2022 | CAY 148/6 v BAH 133/92nd T20I · T20I | CAY | 4* | 1/23 | 0 | Cayman won by 15 runs | George Town | Bahamas in Cayman Islands 2022 |
| 25 Aug 2019 | BER 115/4 v CAY 114Match 12 · T20I | CAY | 3 | 1/14 | 1 | Bermuda won by 6 wickets | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
| 24 Aug 2019 | CAY 66/9 v USA 70/1Match 9 · T20I | CAY | 6 | 0/17 | 0 | United States of America won by 9 wickets | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
| 22 Aug 2019 | CAN 95/2 v CAY 91/7Match 7 · T20I | CAY | 6 | 0/41 | 0 | Canada won by 8 wickets | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
| 21 Aug 2019 | BER 117/4 v CAY 116/9Match 5 · T20I | CAY | 6* | 1/33 | 0 | Bermuda won by 6 wickets | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
| 19 Aug 2019 | CAY 68/8 v USA 60/5Match 4 · T20I | CAY | 7 | 1/7 | 0 | United States of America won by 10 runs (DLS method) | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
| 18 Aug 2019 | CAN 196/6 v CAY 112/7Match 2 · T20I | CAY | 9 | 1/39 | 0 | Canada won by 84 runs | Hamilton | ICC Men's T20 World Cup Americas Region Final 2019 |
