Both these teams will be regarded as having over-achieved at this tournament if they reach the semifinals. This is Canada's first trip out of the group stage of a Gold Cup since 2009, and the team didn't win a game or score a goal at the last two editions of this competition.
It's not unreasonable, therefore, to say this is already a successful Gold Cup for Canada. The team was unbeaten in the group stage, and teenager Alphonso Davies is still the tournament's (joint) top scorer. The brouhaha over French Guiana's dispute with CONCACAF over player eligibility rules could have been an excuse or distraction, but Canada played the two teams expected to beat it in Group A - Costa Rica and Honduras - to draws, qualifying for the quarterfinals on merit, without help or hindrance from the disciplinary action levied against French Guiana.
Canada has done well, but would of course like to do better. The draw has been somewhat kind. Jamaica is not the weakest team in the quarterfinals, but it is not the strongest either. Nor is this Reggae Boyz squad comparable to the team that made the final of the 2015 Gold Cup. That roster was stacked with seasoned pros based at European clubs; in 2017, Jamaica is taking a close look at its domestic player pool, hoping to develop the core of a squad that might eventually lead a successful qualifying bid for the 2022 World Cup.
As such, this Jamaica team has perhaps surpassed expectations by qualifying out of the group stage unbeaten. The relatively unheralded group of players did very well to play Mexico to a scoreless draw in Group C, though there was understandable disappointment that the team was not able to beat El Salvador in its group stage finale.
Neither of these teams is expected to move beyond the semifinals, where it is assumed Mexico will prevail (once it has navigated its quarterfinals against Honduras). But either would enjoy the chance to prove those expectations wrong.
It might not be entirely fair to either team, but whichever one wins this game will be regarded as an unlikely semifinalist and the weakest team remaining in the tournament (yes, even if Mexico loses to Honduras in its quarterfinal - because a team that has beaten Mexico will automatically accrue some respect). The underdog mantle has suited both so far, and one will get the chance to really cause a stir in the July 23 semifinal at the Rose Bowl.
Per livesoccertv.com, here's where to find the game if watching from the USA: