| 16/06/2024 | | NCT5 | | | | National Championships Cayman Islands (East End) I.T.T. (30,1 km) | |
| 11/06/2023 | | NCT5 | | | | National Championships Cayman Islands (East End) I.T.T. (31 km) | |
| 10/07/2022 | | NCT5 | | | | National Championships Cayman Islands (East End) I.T.T. (31 km) | |
| 28/07/2019 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (39 km) | |
| 3/06/2018 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (40 km) | |
| 25/06/2017 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (39 km) | |
| 12/06/2016 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (38 km) | |
| 21/06/2015 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (38 km) | |
| 6/07/2014 | | NCT5 | | | | National Championships Cayman Islands (Frank Sound) I.T.T. (38 km) | |
| 10/11/2013 | | NCT5 | | | | National Championships Cayman Islands (Bodden Town) I.T.T. (45 km) | |
| 7/10/2012 | | NCT5 | | | | National Championships Cayman Islands (Georgetown) I.T.T. (16,1 km) | |
| 16/10/2011 | | NCT5 | | | | National Championships Cayman Islands (Georgetown) I.T.T. (16,1 km) | |
| 10/10/2010 | | NCT4 | | | | National Championships Cayman Islands (Georgetown) I.T.T. (16,1 km) | |
| 18/10/2009 | | NCT4 | | | | National Championships Cayman Islands (South Sound) I.T.T. (16,1 km) | |