CPL PLAYOFF PREVIEW: What you NEED to know for Halifax Wanderers vs. York United | OneSoccer Direct ⤴️

The ascent begins Wednesday night, when the 2025 Canadian Premier League Playoffs kick off with a knockout match between the Halifax Wanderers and York United.

It's York's third straight appearance in this fourth-versus-fifth postseason game, and just the second CPL Playoff match ever played at the Wanderers Grounds.

This matchup, confirmed on Saturday during The Outcome when both sides lost their final regular season match, pits the fourth-place Wanderers against a closely trailing York side. The winner will head west to Alberta for a semifinal qualifer with third-place Cavalry FC on Sunday afternoon.

Halifax are looking for the first home playoff win in club history, having lost their prior outing in the 2023 semifinal qualifier against Pacific FC. In fact, the only win the Wanderers have in any kind of postseason was in the group stage of the 2020 CPL season, the truncated competition played behind closed doors in Prince Edward Island, known as the Island Games.

The Wanderers head into Wednesday's game in so-so form, having lost to Atlético Ottawa on Saturday. They posted a 2-1-2 record in the last five games of the regular season, and a 4-2-4 record in the last 10. At home, though, on the familiar grass pitch of the Wanderers Grounds with the atmosphere behind them, they've been excellent all season. They won seven games and picked up 24 points in Nova Scotia this season, and with this being their only potential home game in the playoffs, they have to make use of it now.

York, meanwhile, return to the playoffs aiming for their second postseason win. Last year, they finished fourth and hosted this knockout game, beating Pacific FC 2-0 before bowing out on penalty kicks against Atlético Ottawa.

These two sides each have something to prove on Wednesday, after both failing to climb higher up the table. The Wanderers came into this season bullish, intending not just to get back to the playoffs after missing in 2024, but challenge for silverware. They fell short of their ambition in the regular season, but still have a chance to challenge for the North Star Cup.

Gheisar has spoken openly about how this year's Wanderers team feels different from the one that made the playoffs in 2023 and lost at home. He called that side a little naïve, but his team is now more mature — and has also added the experience of a player like Thomas Meilleur-Giguère, who won a CPL championship in 2021 with Pacific.

"The legacy [we're] starting to leave behind is something that's what the ambition of the club is, and frankly the city and the organization deserves," Gheisar told reporters on Tuesday. "We know what happened two years ago, we want to take it further.

"To be able to share this moment with our fans is really special, but the key is that I feel like last time when we were at this position, we had a lot of nerves and we didn't enjoy the moment. It has to be about enjoying it, because you work 28 games to get this game."

The Nine Stripes came into 2025 with a refreshed squad and a new head coach, as Mauro Eustáquio took over in the technical area after spending the last few years as an assistant. They hovered around the middle of the table most of the year, and although two weeks ago they had a chance to finish fourth and play this game at home, they're well prepared to play knockout football on the road. That said, they only have three wins this year against fellow playoff teams, so they haven't necessarily been in great form against the CPL's top sides.

York went to the Wanderers Grounds twice this year, and didn't particularly enjoy their visits. They lost 4-0 in Halifax on Labour Day, but managed a 1-1 draw just over two weeks ago thanks to a second-half Massimo Ferrin equalizer. However, York did beat the Wanderers in the CPL On Tour match in Québec City at the end of May — in a downpour that may resemble the (hopefully less) rainy conditions in Halifax on Wednesday.

"You're talking, potentially, about two of the most aggressive teams when it comes to style of play," Eustáquio said on Tuesday. "We know how aggressive Patrice [Gheisar] trains their team, and that shows in games, but that's something we're aware of.

"But we're known to be the bad guys too. I'm expecting a football match of a lot of individual duels, a football match of small little details, and a football match that's generally going to be in who makes the least amount of mistakes."

For Wednesday night, both clubs are operatinng almost at full strength. The Wanderers are still missing winger Jason Bahamboula, but Gheisar said that Vitor Dias is a possibility to return pending last-minute testing. York, meanwhile, are without centre-back Nyal Higgins as well as midfielder Leonel López, which is a major blow. However, Ferrin is set to return after missing last weekend, and Orlando Botello is a game-time decision but is likely to be available in some capacity.

These two clubs have had some outstanding battles over the years, many of them at the Wanderers Grounds. This one, however, is the biggest.

After a 28-game regular season, it comes down to just 90 more minutes. One team will move on to face Cavalry. The other goes home.