Canada were in prime position to make the semifinals of the Concacaf Nations League following their 2-1 win over Jamaica earlier this month, but they suffered a shock exit after a 3-2 defeat in the home leg on Tuesday.
The future now looks uncertain for Mauro Biello's men, whose hopes of making the 2024 Copa America have taken a substantial hit, although they will have another bite at the cherry next year.
Here is a look at how the Canada Men's National Team performed in the recent Nations League.
As one of four pre-seeded nations, Canada did not have to go through the group stage in the 2023-24 edition of the Concacaf Nations League, instead advancing directly to the competition's quarter-finals.
They were drawn against Jamaica, who topped League AB with three wins and a draw from four matches and it was always going to be a tough contest.
But Canada quashed any major qualms in the first leg, prevailing 2-1 at Independence Park in Kingston thanks to goals from Jonathan David and Stephen Eustaquio either side of Shamar Nicholson's strike in the 56th minute.
And ahead of the second leg at Toronto's BMO Field, Canada should have been in a confident mood about progressing to the last four.
Things were looking good to begin with as Alphonso Davies created some breathing space on aggregate with a 25th-minute opener but a disastrous second half followed for Canada.
They conceded three times in the space of 16 minutes, culminating in a dubious penalty tucked away by Bobby De Cordova-Reid after Eustaquio's handball.
That handball could be debated but the bottom line is Canada were not good enough in that second period, having failed to make the most of their 17 shots in the game and lacking composure to see the result out.
Speaking after the second-leg defeat to the Reggae Boyz, Canada goalkeeper Milan Borjan said: "We've got to sit down all together, look each other in the eyes and see what went wrong. Because this is unacceptable.
"This team, to have players like that, to do something like this, it's not acceptable.
"I'm very very angry."
Not only did the Jamaica defeat end Canada's Nations League hopes but it has also put a sizable dent in their Copa America 2024 aspirations.
The two-legged loss means Canada have missed out on an automatic qualification berth for the 2024 Copa America in the USA next summer.
Along with the competition's other quarter-final losers, they will still have the opportunity to qualify for Copa America 2024 next March but it leaves the nation in a precarious position.
There will be 16 teams involved at the Copa America next year with ten coming from Conmebol and six coming from Concacaf.
Jamaica, Mexico, Panama and the USA have already qualified from Concacaf and there are two spots up for grabs in the play-in round.
One thing is for sure, there is plenty for Canada to sort out with a home World Cup on the horizon in 2026.
It would be no exaggeration to say Canada are in a bit of a freefall right now.
The defeat to Jamaica in the Nations League quarter-finals is the latest setback in what has been a pretty turbulent time for the team.
After losing all three of their group games at the 2022 Qatar World Cup, things have gone from bad to worse.
They slipped to a 2-0 defeat to the USA in the last edition of the Nations League before a quarter-final loss to the same opponents in the Concacaf Gold Cup.
Head coach John Herdman then stepped down in August to take the Toronto job and Biello was installed as interim head coach.
His tenure began with a 4-1 friendly loss to Japan but he showed signs of promise in the two-legged clash with Jamaica, at least until the second half at BMO Field.
Biello came under fire for the changes he made in the second leg against Jamaica, in particular his triple change after 74 minutes, and it remains to be seen whether or not he will take charge of Canada in the long term.
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