The Centennial Cup was first offered in 2005 as a tournament for lower division Master's, Over 45 and Over 55 teams to coincide with the celebration of the 100th year of soccer in Calgary. The Villains Alumni Soccer Club donated the current trophy in 2008 to award to the tournament's champion. The Centennial Cup is a single-elimination tournament held throughout the Outdoor season. Teams are eligible for the competition if they are registered outdoor teams in Master's 2 or lower; Over 45B or lower or any Over 55 team.
The Genesis Land Dogs have been the most successful team in the competition, winning back-to-back tournaments in 2009 and 2010. Due to the Calgary floods, the 2013 tournament was cancelled mid-season and no champion was determined.
| Centennial Cup - Registered Teams | |||||||
| Division | 2012 | 2013 | 2014 | 2015 | 2016 | Titles | Finalists |
| Master's 2 | 6 | 8 | 6 | 5 | 4 | 2 | 1 |
| Master's 3 | 1 | 3 | 3 | 2 | 3 | 0 | 1 |
| Master's 4 | 2 | 3 | 0 | 0 | 1 | 1 | 0 |
| Over 45B | 6 | 5 | 4 | 4 | 3 | 1 | 1 |
| Over 45C | 0 | 1 | 0 | 2 | 1 | 0 | 0 |
| Over 45D | 0 | 0 | 1 | 0 | 0 | 0 | 0 |
| Over 55 | 0 | 0 | 2 | 2 | 1 | 0 | 1 |
| Total | 15 | 20 | 16 | 15 | 13 | ||
