| 2026-09-27 | T20I | Bermuda v Cayman Islands | 101/9 · 59 | Bermuda won by 42 runs | Jimmy Powell Oval |
| 2026-09-24 | T20I | Cayman Islands v Bahamas | 215/3 · 84 | Cayman Islands won by 131 runs | Jimmy Powell Oval |
| 2026-09-23 | T20I | Bermuda v Cayman Islands | 113 · 115/8 | Cayman Islands won by 2 wickets | Jimmy Powell Oval |
| 2026-09-23 | T20I | Cayman Islands v Bermuda | 143/5 · 149/0 | Bermuda won by 10 wickets | Jimmy Powell Oval |
| 2026-03-15 | T20I | Argentina v Cayman Islands | 114/8 · 116/4 | Cayman Islands won by 6 wickets | Jimmy Powell Oval |
| 2026-03-14 | T20I | Suriname v Cayman Islands | 85/5 · 86/1 | Cayman Islands won by 9 wickets | Jimmy Powell Oval |
| 2026-03-12 | T20I | Cayman Islands v Mexico | 187/3 · 94 | Cayman Islands won by 93 runs | Jimmy Powell Oval |
| 2026-03-11 | T20I | Suriname v Cayman Islands | 92/7 · 96/1 | Cayman Islands won by 9 wickets | Jimmy Powell Oval |
| 2026-03-09 | T20I | Mexico v Cayman Islands | 94/9 · 95/1 | Cayman Islands won by 9 wickets | Jimmy Powell Oval |
| 2026-03-08 | T20I | Argentina v Cayman Islands | 98 · 102/0 | Cayman Islands won by 10 wickets | Jimmy Powell Oval |
| 2025-06-22 | T20I | Cayman Islands v Bahamas | 167/5 · 118/7 | Cayman Islands won by 49 runs | Maple Leaf North-West Ground |
| 2025-06-21 | T20I | Bermuda v Cayman Islands | 139/2 · 142/1 | Cayman Islands won by 9 wickets | Maple Leaf North-West Ground |
| 2025-06-19 | T20I | Canada v Cayman Islands | 81/0 · 39/5 | Canada won by 42 runs | Maple Leaf North-West Ground |
| 2025-06-18 | T20I | Cayman Islands v Bermuda | 121/9 · 126/3 | Bermuda won by 7 wickets | Maple Leaf North-West Ground |
| 2025-06-16 | T20I | Canada v Cayman Islands | 162/5 · 103/9 | Canada won by 59 runs | Maple Leaf North-West Ground |
| 2025-06-15 | T20I | Cayman Islands v Bahamas | 183/7 · 145/7 | Cayman Islands won by 38 runs | Maple Leaf North-West Ground |
| 2025-06-13 | T20I | Canada v Cayman Islands | 236/6 · 110/6 | Canada won by 126 runs | Maple Leaf North-East Ground |
| 2025-06-12 | T20I | Bermuda v Cayman Islands | 172/7 · 142 | Bermuda won by 30 runs | Maple Leaf North-East Ground |
| 2025-04-26 | T20I | Cayman Islands v Canada | 122/8 · 125/0 | Canada won by 10 wickets | Jimmy Powell Oval |
| 2025-04-24 | T20I | Cayman Islands v Bahamas | 175/2 · 96/5 | Cayman Islands won by 79 runs | Jimmy Powell Oval |
| 2025-04-23 | T20I | Canada v Cayman Islands | 165/6 · 71 | Canada won by 94 runs | Jimmy Powell Oval |
| 2025-04-20 | T20I | Bermuda v Cayman Islands | 137/5 · 107/8 | Bermuda won by 30 runs | Jimmy Powell Oval |
| 2025-04-19 | T20I | United States of America v Cayman Islands | 186/6 · 107/7 | United States of America won by 79 runs | Jimmy Powell Oval |
| 2024-12-16 | T20I | Bermuda v Cayman Islands | 139/6 · 126/9 | Bermuda won by 13 runs | St Albans Club |
| 2024-12-15 | T20I | Cayman Islands v Argentina | 116 · 94 | Cayman Islands won by 22 runs | Hurlingham Club Ground |
| 2024-12-14 | T20I | Cayman Islands v Brazil | 224/1 · 65/9 | Cayman Islands won by 159 runs | St Albans Club |
| 2024-12-12 | T20I | Bahamas v Cayman Islands | 108/5 · 109/0 | Cayman Islands won by 10 wickets | Belgrano Athletic Club Ground |
| 2024-12-11 | T20I | Mexico v Cayman Islands | 85 · 86/3 | Cayman Islands won by 7 wickets | St George's College Ground |
| 2024-12-10 | T20I | Cayman Islands v Suriname | 142/8 · 143/4 | Suriname won by 6 wickets | Hurlingham Club Ground |
| 2024-12-08 | T20I | Cayman Islands v Belize | 151/9 · 107/9 | Cayman Islands won by 44 runs | Hurlingham Club Ground |
| 2024-12-07 | T20I | Cayman Islands v Panama | 124/6 · 41 | Cayman Islands won by 83 runs | St George's College Ground |
| 2023-10-04 | T20I | Canada v Cayman Islands | 196/5 · 30 | Canada won by 166 runs | National Stadium, Karachi |
| 2023-10-03 | T20I | Bermuda v Cayman Islands | 176/6 · 123/8 | Bermuda won by 53 runs | National Stadium, Karachi |
| 2023-10-01 | T20I | Canada v Cayman Islands | 194/6 · 86 | Canada won by 108 runs | White Hill Field |
| 2023-09-30 | T20I | Panama v Cayman Islands | 85/8 · 88/3 | Cayman Islands won by 7 wickets | White Hill Field |
| 2023-03-04 | T20I | Argentina v Cayman Islands | 125/7 · 126/7 | Cayman Islands won by 3 wickets | Belgrano Athletic Club Ground |
| 2023-03-02 | T20I | Cayman Islands v Panama | 138/7 · 126 | Cayman Islands won by 12 runs | Hurlingham Club Ground |
| 2023-02-28 | T20I | Cayman Islands v Bahamas | 125 · 94/8 | Cayman Islands won by 31 runs | St Albans Club |
| 2023-02-25 | T20I | Bermuda v Cayman Islands | 173/3 · 77/9 | Bermuda won by 96 runs | St Albans Club |
| 2019-08-25 | T20I | Bermuda v Cayman Islands | 115/4 · 114 | Bermuda won by 6 wickets | White Hill Field |
| 2019-08-24 | T20I | Cayman Islands v United States of America | 66/9 · 70/1 | United States of America won by 9 wickets | White Hill Field |
| 2019-08-22 | T20I | Canada v Cayman Islands | 95/2 · 91/7 | Canada won by 8 wickets | White Hill Field |
| 2019-08-21 | T20I | Bermuda v Cayman Islands | 117/4 · 116/9 | Bermuda won by 6 wickets | White Hill Field |
| 2019-08-19 | T20I | Cayman Islands v United States of America | 68/8 · 60/5 | United States of America won by 10 runs | National Stadium, Karachi |
| 2019-08-18 | T20I | Canada v Cayman Islands | 196/6 · 112/7 | Canada won by 84 runs | White Hill Field |