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It’s a huge few weeks for League1 Ontario clubs as the L1 Cup Round of 16 takes place, with the remaining Premier Division teams entering play.

Vaughan Azzurri vs St Catharines Roma Wolves – Tuesday, May 14

Vaughan Azzurri will host St Catharines Roma Wolves on Tuesday as a Premier team and a Championship team clash in the L1 Cup Round of 16.

The sides contrast in form significantly; the Azzurri continuing their unbeaten streak with a 1-0 win over ProStars last weekend, while St Catharines sit at the bottom of the Championship having only managed to secure one point out of a possible nine.

It will be some achievement if St Catharines can end the Azzurri’s invincible start to the season, and they will be drawing inspiration from their thrilling 3-2 win against North Mississauga in the First Round of the cup.

Simcoe County Rovers vs Darby – Tuesday, May 14

While reigning Men’s Premier Division champions Simcoe have failed to register a win this season, they have found the net in each of their regular-season fixtures. Jevontae Layne will be seeking his third goal in three consecutive games for the Rovers.

Darby meanwhile have one win in the Men’s Championship this season and have lost twice, but it’s their L1 Cup First Round victory that will give them the most confidence heading into this game.

They convincingly defeated Hamilton United 3-1 in the cup’s return, with Hamilton playing in the Premier Division this season. Perhaps they can take another top-flight scalp on Tuesday.

Guelph United vs The Borough FC – Wednesday, May 15

It’s a massive game for The Borough FC as the League2 side gets a taste of Premier Division opposition when they travel to Guelph United.

The home side conceded a 53rd-minute goal at the weekend to deny them any points against Burlington and will be aiming to get back to winning ways against an underdog side who have one point from two League2 games.

The Borough have already impressed in the L1 Cup having defeated Championship-side Pickering in the First Round; Ancelmo Pascoal scoring the winner in the club’s inaugural game.

North Toronto vs Woodbridge Strikers – Tuesday, May 21

There’s an all-Premier tie next week as Woodbridge Strikers are hosted by a defensively struggling North Toronto outfit.

North Toronto have so far conceded more than double the number of goals that Woodbridge have shipped and are yet to gain a point this season, whereas the Strikers are currently unbeaten with a tie and two wins.

The two sides have already met in the league – a game that saw Woodbridge take a 2-0 victory with a penalty from Ronaldo Marshall and a late goal from Exosse Kadiebue. This makes their second encounter one to certainly keep an eye on.

Scrosoppi vs Burlington – Tuesday, May 22

As per the current division standings, the two best men’s teams in League1 Ontario are meeting for the first time this campaign in the L1 Cup Round of 16.

If either team’s start to the season is anything to go by, and the fact that both these sides reached the Men’s Premier playoffs last year, this matchup could have been an L1 Cup Final in its own right.

Scrosoppi were 5-3 winners in this meeting last year – two sides who earned plenty of plaudits having drastically improved following bottom-half finishes in the 2022 standings – and fans can expect more drama in this year’s match.

Sigma vs BVB IA Waterloo – Tuesday, May 28

A chance to show Premier quality presents itself to Waterloo as they take on top-flight strugglers Sigma.

Waterloo won two of their first three games in the Championship, while Sigma managed to score just one goal in their first trio of matches and are currently bottom of the Premier Division standings.

The boys in black and yellow defeated Windsor City in the First Round to book this tie, thanks to goals from Malachi Ramsay and Wesley Cain, who could be players to watch in the Round of 16.

Alliance United vs Master’s FA – Tuesday, May 28

The unbeaten home side have impressed in the Premier Division so far; currently fourth in the standings with seven points and eight goals.

Their opponents have not been quite as productive in the final third, having scored four goals in three Championship games, and recording one win from their first three games.

Master’s FA have already defeated Premier opposition in the L1 Cup this season, thrashing ProStars 4-1 in the First Round. Alliance, therefore, will not be taking their second-tier opponents lightly.

Blue Devils vs FC London – Wednesday, June 5

The last Round of 16 clash will take place in June, with Blue Devils hosting FC London.

In their first three Championship games, FC London picked up two wins and a loss, leaving them third in the table. If Blue Devils’ mixed Premier Division form continues into next month, then the London side might fancy themselves a ‘cupset’.

The Oakville club have won, tied, and lost in the Premier so far this year, with only one team conceding more goals than them in the first three matchweeks.