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.
3 THINGS TO WATCH
- Battle of strikers: The key question around the Wanderers' attack is what sort of form striker Tiago Coimbra will be in. He started on Saturday against Ottawa and played 83 minutes, but that was his first start since Sept. 6. He missed five games entirely but came off the bench in Winnipeg two weeks ago and scored. Coimbra is the Wanderers' leading scorer with 12 goals this year, so if he's fit after a short turnaround from Saturday, he'll be a difference maker. York, meanwhile, have similar questions around their own striker's form. Julian Altobelli is healthy, but after a red-hot start to the season, he cooled off entirely in the second half. He scored eight goals in the first 14 games, but just two in the latter 14 (though he only started nine of them). Mauro Eustáquio needs more from his star forward in the playoffs if they're to make a deep run.
- Questions around York fitness? The Nine Stripes had some surprises in their starting XI on Saturday, as a few usual starters missed out on the squad entirely. Winger Massimo Ferrin, left-back Orlando Botello, and attacking midfielder Leonel López were out of action with knocks, and their absences were felt. Botello is the type of player that could be critical to playoff football, playing with an edge and getting under opponents' skin on the flank. There's no way Ferrin will want to miss this game, either. He rose to prominence in the CPL with the Wanderers over the last two years, and signed with York before this season to play in his hometown. He's very familiar with the Wanderers Grounds, and scored there as a visitor last time York were there; his explosiveness down the wing would be a major boost for York. Unfortunately, Eustáquio confirmed that López is out, which means York will have to find another way to replicate his creativity through the middle, which they were seriously missing against Forge on Saturday.
- Home field vs. playoff experience: There's no question the Wanderers Grounds boasts one of the best atmospheres in the Canadian Premier League. The Halifax faithful will be out in droves for just the second home playoff game in club history, this time under the lights for a little extra drama. Their previous postseason game in Halifax was a disappointment; despite playing pretty well, they didn't manage to score and lost 1-0 to a late Pacific goal. This time, they'll want to correct that. However, York know this fourth-versus-fifth match better than anybody, since it'll be their third straight appearance here. They won this round at home last year, and proceeded to play an extremely close game with Atlético Ottawa. York are a seasoned team who have been here before, and they play a gritty style of football that could lend itself well to the postseason. It'll be a wet, chilly affair in the Maritimes, but the two clubs have no excuses.
PROJECTED STARTING XIs
Halifax Wanderers: Yesli; Pearlman, Alphonse, Meilleur-Giguère, Mekideche, Timoteo; Callegari, Johnston; Telfer, Coimbra, Rea
York United: Urtiaga; Ferrari, Sturing, Adekugbe, Singh, Botello; Yeates, Kibato; Ferrin, Altobelli, Reid
ALL-TIME SERIES
Halifax Wanderers wins: 9 | York United wins: 8 | Draws: 10
LAST METTING
Oct. 4, 2025 — Halifax Wanderers 1-1 York United
KEY QUOTES
"We need a positive start. We need to show that we're the home team, and we have to control the game with and without the ball. That has to be done if we're playing Ottawa, Forge, York or Cavalry. That's really important." - Halifax Wanderers head coach Patrice Gheisar
"It's an all or nothing. We can't let our emotions play with us too much; it's important that we feel those emotions, it's important we feel the importance of the game, but we have to understand how to ride it. We have our game strategy and we have to stay in it from minute one to 90, and then obviously there's things that change. ... We had to make sure that we're, in a sense, cold-blooded, and understand that the game is not going to be finished until it's finished." - York United head coach Mauro Eustáquio
