The City & District Match Play Championship started in 1939.
Past Winners of the Men's Division:
| Year | Winner | Club |
| 2024 | Dwight Reinhart | Ottawa Hunt |
| 2023 | Brad Goodman | Greensmere |
| 2022 | Jonah O'Connor | Renfrew |
| 2021 | Dwight Reinhart | Ottawa Hunt |
| 2020 | Ryan Sevigny | Eagle Creek |
| 2019 | Jordan Burwash | Public Player |
| 2018 | Brad Goodman | Greensmere |
| 2017 | Justin DeVroom | Rideau View |
| 2016 | Nick Brisbois | Kanata |
| 2015 | Chris Collins | Rideau View |
| 2014 | Robert Mustard | Rivermead |
| 2013 | Curtis Barkley | Cedar Glen |
| 2012 | Steve Houle | Kanata |
| 2011 | Jeff Crowe | Camelot |
| 2010 | Dwight Reinhart | Renfrew |
Past Winners of the Senior Men's Division:
| Year | Winner | Club |
| 2024 | Peter Harrison | Ottawa Hunt |
| 2023 | John Taylor | eQuinelle |
| 2022 | John Taylor | Public Player |
| 2021 | Perry Freda | Madawaska |
| 2020 | Ken Lafreniere | Rivermead |
| 2019 | John Taylor | Public Player |
| 2018 | Tom Henderson | Smiths Falls |
| 2017 | Tom Hossfeld | Hylands |
| 2016 | Robert Irvine | The Meadows |
| 2015 | Rick St. Dennis | Public Golfer |
| 2014 | Tom Hossfeld | Hylands |
| 2013 | Bill Holzman | Rideau View |
| 2012 | Larry Lucas | Outaouais |
Past Winners of the Women's Division:
| 2024 | Teri De Luis | Brockville |
| 2023 | Lise Jubinville | Hylands |
| 2022 | Diane Dolan | Hylands |
| 2021 | Terri De Luis | Brockville |
| 2020 | Margot Greenberg | Hylands |
| 2019 | Lise Jubinville | Hylands |
| 2018 | Lise Jubinville | Hylands |
| 2017 | Lise Jubinville | Carleton |