| Award | 2013 | 2014 | 2015 | 2016 |
| Trailblazer | Dick Smith | Kenny Boyce | Linda Burndorfer | Shandi Strong |
| Community Leader (individual) | Chad Smith | n/a | Jonathan Niemczak | Michelle McHale |
| Community Leader (organization) | n/a | REEL Pride | Pride Winnipeg | Rainbow Pride Mosaic |
| New Business | White Lotus Pet Spa | Wookey Films | The Planit Restaurant & Lounge | Oh Doughnuts! |
| Corporate Ally | RBC | Delta Winnipeg | MTS | TD Bank Group |
| Student | Jared Star | Evan Wiens | Evan Maydaniuk | Hayato Nakabayashi |
| Tourism & Hospitality | n/a | n/a | n/a | Alt Hotel |
| Award | 2017 | 2018 | 2019 | 2020 |
| Community Builder | Our Own Health | Scott Carman | Allan Gray | Robynne Kazina |
| Entrepreneur of the Year | Kevin Selch, Little Brown Jug | Ro Mills, Get Your Joey | Alex Varricchio, UpHouse | Gloria Sawatzky |
| Corporate Ally | APTN | Home Depot | RBC | Duboff, Edwards & Schachter Law |
| Employer of the Year | n/a | n/a | Eadha Bread | Little Brown Jug |
| Chamber Member of the Year | New in 2020 | New in 2020 | New in 2020 | Capital Grill |
| Student | Shayne Reitmeier | Tyler Andrade | n/a | n/a |
| Tourism & Hospitality | Fairmont Hotel | Festival du Voyageur | n/a | n/a |