York9 FC, HFX Wanderers FC and Cavalry FC have all advanced to the second round of the 2019 Canadian Championship. York9 FC have advanced to meet FC Edmonton, HFX Wanderers FC of Halifax have advanced to meet Valour FC of Winnipeg, and Cavalry FC of Calgary have advanced to meet Forge FC of Hamilton. 
 
This marks the first year that the expanded Canadian Championship features 13 teams across five rounds, with the two-leg Qualifying Round 1 played 15 and 22 May. The two-leg Qualifying Round 2 will played across back-to-back midweek matches on 4-5 June and 12 June.
 
HFX Wanderers FC of the Canadian Premier League and Vaughan Azzurri of League1 Ontario scored three goals each across the two-leg series, but the HFX Wanderers advanced on account of their three away goals in the first leg. The HFX Wanderers won the first leg away 3:2, but lost the second leg at home 0:1. In the second leg, it was a Ryan Raposo shot that found the back of the net, albeit it was recorded as an won goal after the goalkeeper mishandled the ball.
 
York9 FC of the Canadian Premier League won their series 1-0 over AS Blainville of the Première ligue de soccer du Québec. Ryan Telfer scored the lone goal of the series in the second leg at York Stadium, a second-half tap in after an Erwann Ofouya save on a Simon Adjei shot.
 
Cavalry FC of the Canadian Premier League won their series 4-1 over Pacific FC, also from the same league. The Calgary team won their away leg 2:0 on 15 May and then their home leg 2:1 on 22 May. In the second leg, Calgary took the lead on a Pacific FC own goal before Julian Büscher made it 2-0; Marcus Haber then replied for Pacific FC.