At this tournament last year, the Jamaicans claimed third place thanks to a 1-0 victory over Panama, while Los Leones del Caribe finished fourth in the group stage with five points.
Match preview
After a rough Copa America campaign this past summer, losing all three of their encounters, McClaren has been entrusted with building this team back up, beginning with a strong showing at this tournament.
The 63-year-old was most recently a part of Erik ten Hag's backroom staff at Manchester United but has not been a head coach on the international stage since being sacked as manager of England in November 2007, when the Three Lions failed to qualify for the 2008 Euros.
McClaren inherits a side that have never lost a Nations League group fixture, finishing top of Group B last year with three wins and a draw.
During the 2023-24 Nations League, Jamaica came back to earn a result in three encounters when conceding the opener while losing their semi-final fixture with the USA (3-1) despite scoring first.
Since that defeat, the Reggae Boyz have won three consecutive matches across all competitions when scoring in the opening half.
Jamaica are winless in their previous two Nations League encounters at Independence Park, playing to a 2-2 draw with Haiti in the group stage last season and losing 2-1 in the opening leg of their quarter-final tie with Canada.
A series of strong defensive performances in the early portion of the previous Nations League season was as good as it got for Cuba in 2023-24.
Yunielys Castillo's men went unbeaten in their first three matches at this tournament a year ago and did not concede a single goal, but they could not find the back of the net in their four group fixtures, losing their final encounter to Honduras 4-0.
Los Leones del Caribe have not been quite as sharp defensively in recent times, losing three of their previous four competitive fixtures, conceding three or more goals in each of those defeats, including an 8-0 drubbing in a friendly versus Russia last November.
Cuba have not won a Nations League encounter away from home since claiming a 1-0 triumph at Barbados in March 2023, when they were in League B.
This team have emerged victorious in their last six encounters at this tournament when finding the back of the net since suffering a 2-1 defeat versus Guadeloupe in June 2022.
They have lost five consecutive matches versus the Reggae Boyz, failing to score in each of those instances, with their previous victory against them in Jamaica occurring in a 2003 friendly at Independence Park (2-1).
Jamaica form (all competitions):
W
W
W
L
L
L
Cuba form (all competitions):
W
D
L
L
W
L
Team News
For his first match in charge of Jamaica, McClaren will not have Leon Bailey at his disposal after the Aston Villa man suffered a knock during a Premier League fixture with Leicester City, with Jamal Lowe of Swansea City taking his place.
In this competition last year, Shamar Nicholson finished as the top goalscorer, finding the back of the net five times, while Demarai Gray and Bobby Decordova-Reid each netted three goals.
From their 1-0 triumph over Nicaragua in March to their 3-1 defeat versus Honduras in World Cup qualifying last June, there were four newcomers in Cuba's starting 11, including Raiko Arozarena, Orlando Calvo, Luis Paradela and Maikel Reyes.
Willian Pozo-Venta was the only Cuban to find the back of the net in the previous Nations League campaign, while Arozarena posted three clean sheets.
Jamaica possible starting lineup:
Blake; Latibeaudiere, Hector, Pinnock; Lembikisa, Palmer, Anderson, Decordova-Reid; Nicholson, Gray; Antonio
Cuba possible starting lineup:
Arozarena; Calvo, Y. Perez, Cavafe, Morejon; D. Reyes, Torres, Hernandez, Matos; Paradela; M. Reyes
We say: Jamaica 1-0 Cuba
The Cubans have proven to be a well-organised defensive unit but have not been able to excel in any other capacity, and we believe the creativity of the Reggae Boyz will eventually find a way through what appears to be a one-dimensional team.