Les Rouges didn't progress beyond this stage in the last two editions of the competition and last made it into the semi-finals in 2007.
However, expectations are high this year as the side boasts incredible quality and swatted aside Haiti and Martinique in the group.
Los Ticos, meanwhile, came through Group C unscathed, winning all three of their fixtures against Jamaica, Suriname and Guadeloupe with a combined score of 6-2.
Costa Rica vs Canada Head-To-Head
There have been 21 clashes between the sides in the past, with Costa Rica winning twice as many games (8) as Canada (4).
A total of nine games have ended in draws, including their last two encounters, both of which came in the 2015 and 2017 Gold Cups.
Costa Rica Form Guide (all competitions): D-L-W-W-W
Canada Form Guide (all competitions): W-W-W-W-D
Costa Rica vs Canada Team News
Los Ticos will be without goalkeeper Leonel Moreira as he's suspended from the clash after getting sent off against Jamaica.
Head coach Luis Suarez has two other choices, although Esteban Alvarado, who came in for Moreira after his sending off, is more likely to start.
On the bright side, central defenders Francisco Calvo and Kendall Waston return from their own suspensions and will be available for selection again.
Suspended: Leonel Moreira
The Reds were dealt an injury blow in their last match after Ayo Akinola was ruled out for the remainder of the tournament.
Cyle Larin is also unavailable after hobbling off in the game against the USA with a leg injury.
The return of influential midfielder Stephen Eustaquio from a yellow-card suspension will be a boost.
Injured: Ayo Akinola, Cyle Larin
Costa Rica vs Canada Predicted XI
Costa Rica (4-3-3): Esteban Alvarado; Yael Lopez, Giancarlo Gonzalez, Oscar Duarte, Keysher Fuller; Allan Cruz, David Guzman, Bryan Ruiz; Alonso Martinez, Joel Campbell, Ariel Lassiter.
Canada (3-4-1-2): Maxime Crepeau; Alistair Johnstone, Steven Vitoria, Kamal Miller; Richie Laryea, Liam Fraser, Samuel Piette, Tajon Buchanan; Junior Hoilett; Lucas Cavallini, Theo Corbeanu.
Costa Rica vs Canada Prediction
Canada have been really impressive in the Gold Cup so far and only a lapse in defense cost them the game against the United States in their final group fixture.
The loss of their two main strikers, Larin and Akinola, is obviously a huge blow, but the Reds still have a quality side and can see off Costa Rica.
Prediction: Costa Rica 1-2 Canada