An own-goal in injury time back in March enabled La Roja to claim victory for the first time under new manager Eduardo Berizzo, 3-2 against Paraguay, while the Cubans performed well in League B of the CONCACAF Nations League, defeating Guadeloupe 1-0 on the final matchday to earn a spot in the Gold Cup later this month and promotion into League A of the next Nations League.
Match preview
It has been a difficult eight years for Chilean football, missing out on back-to-back World Cups, with its golden generation not getting any younger.
While we should see some familiar faces dawn the colours of La Roja again this weekend, we are likely to be introduced to some of the new blood in Chile, as 17 players selected have fewer than 10 international caps for the national team.
Qualification for the 2026 finals begins in September, and Berizzo has three matches this month to try and see if this crop of players, many under 30, could be the right mix that are capable of taking them back to the World Cup for the first time since 2014.
Their last match against Berizzo's former team, Paraguay, was the first time that Chile had found the back of the net since he took charge, ending a five-match winless and goalless run in the same instance.
Sunday will only be the third time they battle Cuba in an international fixture, with the Chileans beating them twice in 2007, 3-0 and 2-0, in the span of a week.
A program that has seen its share of struggles and players defecting to other countries over the years seems to have something positive brewing, with the Cubans unbeaten in their last seven fixtures.
Los Leones del Caribe have only conceded once in its last five international encounters while allowing fewer goals (three) than anyone in League B of the CONCACAF Nations League.
To find this successful formula, manager Pablo Elier Sanchez has called in several players based abroad and outside of the official Cuban sports system, and the gamble has paid off, with this team showing much more cohesion and quality than those from years past.
The Cubans have a tough draw at the Gold Cup as their group features Canada and Guatemala and a soon-to-be-determined team, and all of their international victories over the past two years have come against teams currently ranked below them according to the FIFA rankings, with their previous triumph coming against a side who are not members of FIFA (Guadeloupe).
Sunday will mark the first time since 2012 that Cuba will face a South American opponent in an international fixture, narrowly losing 1-0 to Bolivia in February of that year.
Chile friendly form:
Chile form (all competitions):
L
L
D
L
D
W
Cuba friendly form:
Cuba form (all competitions):
W
W
W
D
W
W
Team News
Alexis Sanchez, the record goalscorer for Chile (51), is tied with Gary Medel for the most all-time appearances with the national team (153), while Arturo Vidal is two away from reaching 140.
Vidal can match Ivan Zamorano for the fifth-most goals with the national team should he find the back of the net in this one, while Maximiliano Rodriguez, Cesar Perez, Javier Altamirano, Matias Zaldivia, Joaquin Gutierrez and Cristobal Campos will all be seeking their first cap with the senior side.
Paulo Diaz and Sanchez both netted in their previous friendly versus Paraguay though it was an own-goal from keeper Anthony Silva which gave them the victory in stoppage time, 11 minutes after Diaz had been sent off.
Aldair Ruiz and Romario Torres were the only Cubans selected for this international window without a cap for the senior side, with Jorge Corrales of Tulsa in the United States Soccer League their most experienced player chosen at 42 caps.
Yasniel Matos had the only strike in their triumph versus Guadeloupe the last time out as Raiko Arozarena picked up a clean sheet in just his third appearance between the sticks, replacing Sandy Sanchez, who started in their 1-0 victory over Barbados.
Arichel Hernandez emerged as a player to watch at the Nations League for Cuba, scoring four goals, including a hat-trick in a 3-1 win over Antigua and Barbados, while strikers Luis Paradela and Maikel Reyes have each netted eight times for the national team.
Chile possible starting lineup:
Arias; Soto, Gutierrez, Maripan, Suazo; Vidal, Medel, Mendez, Nunez; A. Sanchez, Davila
Cuba possible starting lineup:
S. Sanchez; Corrales, Piedra, Vazquez, Mendez; A. Hernandez, Caballero, Perez; Reyes, Paradela, Pozo-Venta
We say: Chile 3-0 Cuba
Cuba have come a long way over the past year but have not faced any formidable opponents or teams as experienced with the ability to score like Chile, and this could be one of those games where once the Chileans find the mark, the floodgates could open.