Jamaica's senior Reggae Boyz achieved what will be remembered as one of the most remarkable comebacks in Concacaf Nations League history, as they stunned Canada 3-2 in a lively second-leg League A quarterfinal encounter, at BMO Field in Toronto, on Tuesday night.

Spurred by a brace from Shamar Nicholson, who scored in the 63rd and 66th minutes to take his international tally to 16 goals, and a 78th-minute Bobby Reid penalty, the Jamaicans overturned a 1-2 deficit to win on the away goal rule. The tie ended 4-4 on aggregate.

Alphonso Davies (25th) and Ismael Kone (69th) got Canada's goals.

Heimir Hallgrimsson's side in the process of securing their spot in the Nations League semi-finals, as well as the prestigious CONMEBOL Copa America 2024, rewrote the history books, as it was their first ever victory on Canadian soil, and the first time that the Caribbean side was scoring three goals against a North American opponent on their turf.

The Reggae Boyz are now set to lock horns against United States in one semi-final, in March, while Mexico, who overturned a two-goal deficit and defeated Honduras 4-2 on penalty, will meet Panama in the other, much like they did in this year's Gold Cup final.

Meanwhile, Canada will face Trinidad and Tobago in one Play-In fixture, while Costa Rica and Honduras will meet in the other. The winner of those Play-In contests will qualify for next year's Copa America.

After taking a 2-1 lead in their rain-interrupted first-leg clash at the National Stadium, Canada pressed that ascendancy at the start in the packed BMO Field and could have easily extended their advantage in the first 15 minutes, but for two incredible saves from Jamaica's goalkeeper Andre Blake.

The host inevitably got their breakthrough when Davies met a cross from the left and fired a shot that was initially deflected by Blake but spun backward into net.

Jamaica needed a response and minutes after should have pulled level after the re-start, but Leon Bailey's dry spell in the national setup continued, as he slammed his left-footed shot into crossbar.

The equalizer eventually came three minutes past the hour when Damion Lowe showed grit to dispossess an opponent and slipped a pass through for Nicholson, who rifled a right-footer past Canada's custodian Milan Borjan.

With the momentum now in their favour, the Jamaicans took the lead three minutes later on a well-worked counterattack in which Reid found Demarai Gray, and the former Everton mam swept a pass across the 18-yard yard box for the towering Nicholson to finish from close range.

However, their celebrations were short-lived, as Canada regained the advantage on aggregate soon after when Davies served up a cross for Kone to steer past Blake.

Still, the Jamaicans pressed and got the golden opportunity to not only pull level, but more importantly go ahead on the away goal rule, when Stephen Eustaquio handled an intended cross from Lowe inside the danger area. Reid stepped up to take the pressure-packed 12-yard kick and calmly converted to silent the home fans, while the small section of Jamaican supporters went into frenzy.

From there, Jamaica only needed to defend their lines and if that wasn't pressure enough, given their tendency to concede late goals, the task became even more difficult when Gray was shown a second yellow and given marching orders in the 84th minute.

Despite the numerical disadvantage, the Boyz managed to absorb all that Canada threw at them in the final minutes plus nine minutes of added time to snare a momentous victory.

Jamaica's senior Reggae Boyz Head Coach Heimir Hallgrimsson rued his team’s missed opportunities along with a lapse in concentration that proved their undoing, as they will have to overturn a one-goal deficit if they intend to progress to the Concacaf Nations League semi-final, as well as next year's Copa America, after they went down 1-2 to Canada in their opening quarter-final leg at the National Stadium on Saturday.

Jonathan David sent Canada in front in the 45+1, before Shamar Nicholson added to his rich Nations League scoring form, with a 56th-minute strike. However, poor defending by the Jamaicans allowed Stephen Eustaquio (86th) to notch the decisive goal and put Canada in the driver's seat heading into Tuesday's second leg at the BMO Field in Toronto.

"It was really hot, so the tempo understandably wasn't high. In a game like this it's about keeping focus, they lost focus, and we didn't punish them, and we lost focus, and they punished us. At this level when you don't take your chances you get hurt and that was the end result," Hallgrimsson said in a post-game interview.

Jamaica started the contest, which was pushed back from Friday due to inclement weather, spiritedly in bright sunny conditions, as they showed some degree of enterprise in the early exchanges and should have opened the scoring in 15th minute. This, as Leon Bailey breached Canada's defence, but dragged his left-footed effort wide of the target in a one-on-one situation with goalkeeper Milan Borjan.

Canada also had an early opportunity of their own through David, whose effort was kept out by Reggae Boyz captain Andre Blake in goal.

The Canadians continued their probe and almost broke the deadlock in the 32nd, as Cyle Larin was allowed time and space to release a right-footer from outside the 18-yard box, but Blake again proved equal to the task.

Canada used the channels well for the service and had a few more half chances but were still unable to break Jamaica's resistance. 

Bailey should have put the Jamaicans in front in the 40^th when he arrived at the far post to meet Bobby Reid's weighted corner, but the effort slammed into the left upright. 

The Jamaicans later paid for that missed opportunity, as Larin turned his marker and played a pass inside for David to tap in.

Canada should have added another in stoppage time, when David produced a tidy run down left channel and found Larin, who had enough time and space to pick a spot from dead centre of the 18-yard box but steered right-footer wide.

The North Americans picked up where they left off on the resumption and almost doubled the lead four minutes in, but David's well-struck effort from almost 20-yards out was parried by Blake.

Jamaica came into their own and pulled level when a quickly taken freekick from Reid sent Nicholson in behind Canada's defence and the towering striker made no mistakes with a firmly struck effort. Though initially flagged offside, the goal stood via the VAR review.

From there, the contest remained evenly poised and could have gone either way in the latter stages, but it was Canada, who inevitably found the winner.

Richie Laryea’s dashing run down the right channel dragged Jamaica’s defence and opened up space for Eustaquio to sweep home the perfect cut-back pass from deep inside the 18-yard box.