The two nations, who are separated by two points in Group A, have never faced each other in either a competitive or no-competitive fixture before.
Match preview
Canada made history on Wednesday as they secured their first-ever victory at the Copa America, battling past 10-man Peru to claim a hard-fought 1-0 win in stifling temperatures of almost 100 degrees at Children's Mercy Park in Kansas.
The dismissal of Peru defender Miguel Araujo for a stud-showing tackle just before the hour mark helped swing the contest in Canada's favour, and in-demand talisman Jonathan David marked his 50th cap with the decisive goal scored 16 minutes from time.
Canada failed to win or even score in their first three games under new head coach Jesse Marsch, albeit friendly fixtures against the Netherlands (4-0) and France (0-0) before losing 2-0 to Argentina last week, but there were plenty of positives for Marsch to take from their historic victory over Peru.
The Reds have climbed to second place in Group A with three points and victory on Sunday would secure their spot in the quarter-finals. A draw could also be enough to progress as long as Peru do not pull off an almighty upset against group leaders Argentina.
Canada's win over Peru was just their second against a CONMEBOL opponent this century after beating Colombia in the 2000 Gold Cup final. The Reds, ranked 48th in the world by FIFA, can write their names in the history books once again with success over a Chile outfit who are yet to set the world alight at this summer's tournament.
Two-time Copa America champions Chile (winners in 2015 and 2016) are in danger of failing to advance from the group stage for the first time since 2004 as they have only picked up one point from their opening two Group A fixtures against Peru and Argentina.
La Roja played out a goalless stalemate with Peru on matchday one before suffering a narrow 1-0 defeat to reigning champions Argentina on Wednesday, with substitute Lautaro Martinez netting an 88th-minute winner.
Ricardo Gareca, one of only four men to coach at five different Copa Americas, admitted after the match that it "hurt" to lose via a late goal and has insisted that his Chile side "are going to leave everything" on the pitch in Sunday's crucial contest with Canada.
Chile currently sit third in Group A, level on points with Peru in fourth and two points behind second-placed Canada. La Roja must beat Canada and also better the result of Peru against Argentina to secure a top-two finish.
One of Gareca's biggest tasks ahead of Sunday's match is to rediscover Chile's form in the final third; La Roja are yet to score at this summer's tournament - registering just four of their 14 shots on target - having previously netted eight goals in Gareca's first three international matches in charge earlier this year.
Canada Copa America form:
L
W
Canada form (all competitions):
L
W
L
D
L
W
Chile Copa America form:
D
L
Chile form (all competitions):
L
W
L
W
D
L
Team News
Canada reaped the rewards from Marsch making a triple substitution at half time in the win over Peru; Derek Cornelius, Liam Millar and Ismael Kone were all taken off early and are at risk of dropping to the bench on Sunday.
Cornelius could be replaced in central defence by Kamal Miller, while Richie Laryea may keep his spot at left-back which would allow Bayern Munich's Alphonso Davies to play further forward on the left flank.
Cyle Larin (29) and David (27) are Canada's top-two record goalscorers and are expected to continue their partnership in attack, while either Tajon Buchanan or Jacob Shaffelburg could be handed a start on the right wing at the expense of Millar.
As for Chile, Gareca is likely to consider making a couple of changes, with Ben Brereton Diaz pushing to start in attack ahead of either Eduardo Vargas or Victor Davila.
Twenty-year-old Midtjylland winger Dario Osorio could retain his spot on the right, while 35-year-old Alexis Sanchez, Chile's all-time record goalscorer (51) and appearance-maker (165) is set to continue in the number 10 role.
Like Sanchez and Davila, Erick Pulgar is just one booking away from a suspension, but the midfielder is expected to start again alongside either Rodrigo Echeverria or Marcelino Nunez.
Canada possible starting lineup:
Crepeau; Johnston, Bombito, Miller, Laryea; Osorio, Eustaquio; Buchanan, David, Davies; Larin
Chile possible starting lineup:
Bravo; Isla, Lichnovsky, Diaz, Suazo; Nunez, Pulgar; Osorio, Sanchez, Brereton Diaz; Vargas
We say: Canada 1-1 Chile
A closely-fought contest between two teams with contrasting levels of experience on the Copa America stage could be on the cards this weekend. Although Chile - who must win to keep their knockout hopes alive - will be regarded by some as slight favourites, we can see an upbeat Canada side claiming at least a share of the spoils this time around.