| Played | Trinbago Knight Riders Won | Jamaica Tallawahs won | Tie | No Result | Abandoned |
| 19 | 10 | 9 | 0 | 0 | 0 |
| Date | Winner | Won By | Venue |
| 9 September 2020 | Trinbago Knight Riders | 9 wickets | Trinidad |
| 1 September 2020 | Trinbago Knight Riders | 19 runs | Trinidad |
| 21 August 2020 | Trinbago Knight Riders | 7 wickets | Trinidad |
| 13 September 2019 | Trinbago Knight Riders | 41 runs | Jamaica |
| 6 September 2019 | Trinbago Knight Riders | 22 runs | Trinidad |
| 19 August 2018 | Trinbago Knight Riders | 4 wickets | Florida |
| 10 August 2018 | Jamaica Tallawahs | 4 wickets | Trinidad |
| 26 August 2017 | Trinbago Knight Riders | 36 runs | Jamaica |
| 9 August 2017 | Jamaica Tallawahs | 4 wickets | Trinidad |
| 5 August 2016 | Jamaica Tallawahs | 19 runs (DLS) | St Kitts |
| 18 July 2016 | Jamaica Tallawahs | 19 runs | Jamaica |
| 4 July 2016 | Jamaica Tallawahs | 7 wickets | Trinidad |
| 23 July 2015 | Trinbago Knight Riders | 27 runs | Trinidad |
| 19 July 2015 | Trinbago Knight Riders | 7 runs | Trinidad |
| 9 July 2015 | Jamaica Tallawahs | 50 runs | Jamaica |
| 13 August 2014 | Jamaica Tallawahs | 4 wickets | St Kitts |
| 26 July 2014 | Trinbago Knight Riders | 13 runs | Trinidad |
| 18 August 2013 | Jamaica Tallawahs | 3 wickets | Jamaica |
| 7 August 2013 | Jamaica Tallawahs | 5 runs | Trinidad |
*Last updated after CPL 2020
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