Over a historic last five years for the Canadian men's national team, only a handful of results can truly be considered disappointing. On June 29, 2019, for example, Canada were up 2-0 at half-time against Haiti in the 2019 Concacaf Gold Cup quarter-finals. In 26 calamitous second-half minutes, they conceded three times, largely due to their own defensive errors, and a once-promising tournament came to a humbling conclusion. It was a horror show that in many ways repeated itself in November, the last match that Canada played. In the quarter-finals of the 2023-24 Concacaf Nations League Canada were again up by two goals, this time on aggregate, entering the second half at BMO Field against Jamaica. An awful 15 minutes in the second half saw Jamaica score three times and eliminate Canada on away goals. Winning that match would have secured Canada a spot at the 2024 Copa América. Instead, they are now forced to play in a critical one-match play-in against Trinidad and Tobago on Saturday in Frisco, Texas for a spot at the prestigious tournament. The legacy of that 2019 loss to Haiti, however, is that Canada quickly learned the harsh lessons they were taught. Just four months later, they defeated the United States for the first time in 34 years 2-0 at BMO Field, a result and performance that instilled the belief that this team was capable of something special. Now, four months after their loss to Jamaica, they have a chance against Trinidad and Tobago to pick up a similarly monumental result -- and show, like they did back in 2019, that this program can take a humbling result in stride and use it to fuel their upward trajectory. The signs are already there that the difficult lessons from that second half in November are being put into action. The squad that interim head coach Mauro Biello named for this match, for example, is a clear changing of the guard from the last cycle. Against Trinidad and Tobago there will be no Milan Borjan, no Steven Vitória, no Mark-Anthony Kaye, and no Junior Hoilett, while Jonathan Osorio misses out with injury. Every player on this team is under 30, with a clear eye toward the 2026 home World Cup. That was largely the case after the loss to Haiti, with players like Scott Arfield, Will Johnson, Russell Teibert, Marcus Godinho and Jayson Leutwiler receiving fewer and fewer caps and call-ups for the national team after that Gold Cup tournament. The squad called up for the clash with the United States at BMO Field in October 2019 saw Kamal Miller make just his second start, while players who have now become central to the national team's success like Stephen Eustáquio, Richie Laryea and Sam Adekugbe were all introduced or reintroduced to the group after that Gold Cup competition.
Another key lesson from that Haiti match, Alphonso Davies was rarely deployed as a fullback again for Canada after a somewhat disastrous outing at the position while still being just 18 years of age at the time. What tactical and personnel shifts Biello makes against Trinidad and Tobago remains to be seen, but he has to make at least one -- in net as Borjan was not called up. Meanwhile, only two of the five players he brought off the bench against Jamaica are available to him now. One other learning from that Jamaica match was that once Canada did go down, they lacked the depth in attacking options to be able to truly threaten the Reggae Boyz in the dying moments. That should change against Trinidad and Tobago, with strikers Theo Bair (11 goals this season for Motherwell in the Scottish Premiership) and Iké Ugbo (10 goals in the championship between Cardiff City and Sheffield Wednesday) reintroduced to the squad. How this young group deals with the pressure of one of the most important matches in the country's history will be telling. The value of qualifying for the Copa América tournament this summer, of getting to play World Cup champions Argentina in the tournament opener, cannot be overstated. This will be a mental battle first and foremost, knowing what happened in November and making sure to play without fear on Saturday, the way this group has when it is at its very best. They face a Trinidad and Tobago side that while on paper, and in the FIFA rankings (Canada is 50th, the Soca Warriors are 96th ) are not especially close, are still capable of some shock results. The Soca Warriors famously prevented the United States from qualifying for the 2018 World Cup with a 2-1 victory on the final matchday. They are coming off the high of beating the United States again 2-1 in Port of Spain in the second leg of the Concacaf Nations League quarter-finals in November. This match is the perfect opportunity, however, for this Canada group to show that it is capable of learning and adapting under significant pressure. If they can demonstrate that on Saturday, it could be the dawn of a new rise for the Canadian men's national team as they prepare to host the World in 2026.

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