| YEAR | WINNERS | TITLE | |
| 2018 | Moses Yacoob | 2018 Canadian Trup Chaal Team Champion | |
| Mohamed Africk | 2018 Canadian Trup Chaal Team Champion | ||
| Chunny Lall | 2018 World Trup Chaal Team Champion | ||
| Pepe Doondoon | 2018 World Trup Chaal Team Champion | ||
| Pepe Doondoon | 2021 Ontario Rap King (individual Champion) | ||
| 2021 | Neville Dhanai | 2021 Ontario Rap Team Champion | |
| Vishnu Singh | 2021 Ontario Rap Team Champion | ||
| Govind Jagroop | 2021 Ontario Rap Team Champion | ||