Men 4: From 18th April 2023
| Teams | Position | Home Player(s) | Away Player(s) | Result |
|---|---|---|---|---|
| Calgary Winter Club A vs. West Hillhurst A | 1 |
 Matthew Pearson |
Kevin Casey |
3 - 0 15-3, 15-7, 15-7 |
| Calgary Winter Club A vs. West Hillhurst A | 2 |
Trevor Reynolds |
Mark Hefford |
3 - 1 11-15, 15-11, 15-13, 15-10 |
| Calgary Winter Club A vs. West Hillhurst A | 3 |
Bryan Krawchyshyn |
 Vining Wolff |
3 - 0 15-5, 15-7, 15-8 |
| Calgary Winter Club A vs. West Hillhurst A | 4 |
Don Mikalson |
Christophe Altier |
3 - 0 15-3, 15-13, 15-12 |
| Calgary Winter Club B vs. South Calgary Squash Club (WED) | 1 |
Reed McLean |
Mike Meldrum |
3 - 0 15-8, 15-8, 15-9 |
| Calgary Winter Club B vs. South Calgary Squash Club (WED) | 2 |
Joshua Kramer |
 Justin Comfort |
3 - 0 15-7, 15-12, 15-7 |
| Calgary Winter Club B vs. South Calgary Squash Club (WED) | 3 |
Kris Simard |
Alex Bershadsky |
3 - 2 5-15, 15-12, 15-11, 9-15, 15-12 |
| Calgary Winter Club B vs. South Calgary Squash Club (WED) | 4 |
Kevin Brent |
 Alex Altamirano |
3 - 0 15-6, 15-8, 15-6 |