15 June 2026
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Windsor City’s OPL Men’s promotion push turns heads: ‘We haven’t always been the most respected’
A new attacking outlook is fuelling something special in Windsor this year.

By Marty Thompson
Windsor City FC — an inaugural Ontario Premier League club — is used to operating far afield, away from the traditional heavy-hitters in the province’s top league in Toronto, Kitchener-Waterloo, or London. They haven’t always been respected because of this, by their own account.
That is, until this season in OPL 2.
Windsor sits atop the OPL 2 standings through 11 matches with a 7-1-3 record and 24 points. On Saturday, they continued their impressive run with a 3-2 win over Pickering FC – thanks to a hat-trick from golden boot leader Ciaran O’Connor – to maintain sole ownership of the lone OPL 1 automatic promotion place.
“Windsor hasn’t always been the most respected team in the OPL,” said Gabe Poulino, Windsor’s OPL 2 men’s coach. “And I think the guys have taken that to heart this season.”
Their history, which reaches well past the founding of OPL (then League1 Ontario) in 2014, is rich with player development and a deep sense of community in the city of 200,000-odd people… But the results on the field typically leave them mid-table at best. Last year, Windsor picked up just 26 points from 22 matches.
“The difference this year is how we set up from how we finished last season and changing the mentality: We have the talent, we have the capability – we just need the belief we can go out and compete,” Poulino said. “This season, we came out understanding that we’re a good team and that, mentally, we need to be tougher. Every game is in our hands.”
Windsor’s goalscoring has been a particular highlight, thanks to O’Connor and his attacking partner Songmafolo Coulibaly, who currently sit first and second in the OPL2 golden boot race with 10 and nine goals, respectively. O’Connor earned an OPL Men’s Three Stars of the Month award for May after netting six goals in the month.
The pair move freely across the attacking unit, floating and finding space with ease and, in turn, leading to the overwhelming majority of the team’s 30 goals in just 11 matches. A big part of that confidence, Poulino suggests, is their former attacking teammate Jefferson Bosiakali who has
shifted back in the midfield to become one of the division’s best number sixes overnight.
“Last year we really struggled to hold the middle [of the field] – Jefferson has changed that,” Poulino said. “That solidity has really given Songmafalo and Ciaran the confidence to take risks.”
Historically, Windsor has been one of the toughest away days in the OPL. But what’s made Windsor’s season extra special is their own away form. As of this writing, Poulino’s side has outscored opponents 13-1 away from Acumen Stadium, including a 4-0 win over Waterloo
United and another 3-0 victory away to Hamilton United.
Their last match away to Master’s FA, the OPL’s Match of the Week, was another dominant performance that featured confidence that, admittedly, has been missing from Windsor sides in the OPL over the years.
“We never really had the confidence… Going up the road, Toronto has always had massive talent,” Poulino added. “We haven’t really challenged our players: We have to be better and they can be better. Going up to Toronto, you can show off against some of the best players in Canada.”
With the regular season nearly half over, Windsor sits as one of the favourites for promotion to the OPL 1 play and, perhaps, a chance to showcase their newly-established confidence in Ontario’s top tier next season.
“This season, we had the goal to do something very special on behalf of the city,” Poulino concluded. “And that’s a real reason why we’ve played so well – we have a goal.”