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There are some tough starts for our expansion teams as they make their L1 Cup debuts against Premier Division opponents.

Following a hectic ending to the 2025 men’s season with tight promotion and title battles, foes old and new across the Pro-Am pyramid are set to face off again this spring and begin their cup campaigns.

There are two expansion teams in the competition in 2026, and they both have difficult debuts: Richmond Hill travel to Premier Division outfit St Catharines Roma Wolves, while Kingston Sentinels are also on the road to face the newly promoted Unionville Milliken.

Scrosoppi are the current title holders in this tournament, and they have a bye to the second round. They will face the winner of the match between Cambridge United – who were promoted to the Championship – and Inter Toronto Pathway (previously York United Academy).

Vaughan Azzurri, who fell at the final hurdle last year, have been drawn to play either Pickering or Windsor City of the Championship in the second round.

A fresh start

After narrowly missing out on a spot in the Premier Division for 2026 after their Pro/Rel Playoff defeat, The Borough travel to fellow Championship side Whitby.

The Scarborough-based team crashed out at this stage last season against St Catharines, so they will be looking to go further against opponents who made it to the second round in 2025. An exciting matchup against Premier Division champions Woodbridge Strikers awaits the winner of this one.

FC London had a tough time in the top tier last season and were relegated come August. Their cup campaign for this year does not start any easier: they host Oakville, who came fifth in the Premier Division last year. The Championship side did make it to the quarterfinals in this competition last time out, though, so they will be aiming to repeat that same success.

There could be some early upsets on the cards too, with League2 side Rush Canada Academy travelling to North Toronto of the top tier, and the third tier’s Railway City are the home side for their clash against 2021 Premier Division winners Guelph United.

There are several Premier versus Championship matchups, as Sigma host North Mississauga and Simcoe County Rovers travel to Waterloo United. Master’s FA are also on the road against opposition of the same level to face International FC, who it was announced acquired Alliance United’s League1 Ontario licenses on Friday.

Sudbury Cyclones left a winless Hamilton United behind in the Championship last year after they were promoted thanks to a second-placed finish. Redeemer University is the venue for this match, as the latter look to forget a disappointing 2025 and push for a cup run.

This year, once the first two rounds are complete, a new draw will take place to determine the quarterfinal fixtures.