The hosts are currently in fourth place in League A Group B with two points, while the visitors are bottom of the standings with one point after the first two rounds of matches.
Match preview
Cuba kicked off their new Nations League campaign on a fairly promising note, holding the heavily fancied Jamaica to a goalless draw at Independence Park in Kingston last month.
In that match, Los Leones del Caribe were reduced to 10 men moments before the halftime interval and somehow managed to survive immense pressure by the Reggae Boyz, who took a total of 21 shots at goal but failed to find the back of the net with any.
Yunielys Castillo's side followed up that performance with a much better showing against Nicaragua three days later and were on the verge of a 1-0 victory but were forced to settle for a point when Widman Talavera scored an equaliser in stoppage time.
That goal was Cuba's second-ever in League A of this competition, with the previous one coming in a 1-0 win over Suriname last September. However, the result did end their 100% record here at Estadio Antonio Maceo in the Nations League.
The Cubans are now set for a double-header against a familiar foe in Trinidad and Tobago, who they have faced 23 times in the past but have only beaten nine times to date (W9 D2 L12).
The last encounter between these two came in the CONCACAF Gold Cup back in July 2015, a match in which Trinidad and Tobago won 2-0 thanks to first-half goals by Sheldon Bateau and Andre Boucaud.
The Soca Warriors are now in need of a repeat of that performance this week having suffered a heavy 4-0 defeat to Honduras in their opening match of this competition before playing out a disappointing goalless draw at home against French Guiana in round two.
Indeed, those performances were some way from the level of play Derek King's side delivered in their World Cup qualifiers in June, though they have still conceded only one defeat across all competitions since mid-May.
However, it is evident that the Soca Warriors do tend to struggle when playing away, as they have only managed one victory in their last five matches on the road, conceded a total of 15 goals, and failed to score in three games during that period.
Cuba CONCACAF Nations League form:
D
D
Cuba form (all competitions):
L
L
W
L
D
D
Trinidad and Tobago CONCACAF Nations League form:
L
D
Trinidad and Tobago form (all competitions):
W
W
D
W
L
D
Team News
Cuba will have to make do without the services of Yunior Perez for this match due to suspension, which should see Castillo opt for a four-at-the-back formation, with Dariel Morejon and Karel Perez making up the central defensive duo.
Karel Espino netted his first goal in a competitive match for Cuba in the draw against Nicaragua, and he should keep his place as the deepest-lying midfielder, while Onel Hernandez and Daniel Diaz are likely to support Maykel Reyes in attack.
Meanwhile, Trinidad and Tobago are set to welcome back two veterans for this match in the shape of Joevin Jones and former captain Kevin Molino, who last featured for the side in the 2023 Gold Cup in the USA.
King's selection for this double-header also includes Toronto FC attacker Tyrese Spicer, who was the top pick from last year's MLS Draft, in place of AEK Athens striker Levi Garcia, who has been excluded having only recently returned from injury.
Cuba possible starting lineup:
Morgado; De la Cruz, Morejon, Perez, Blanco; Espino, Diaz, Cordero, Matos, Hernandez; Reyes
Trinidad and Tobago possible starting lineup:
Smith; A Jones, David, Garcia; Ramparsad, Gilbert, Gill, J Jones; Telfer, Spicer, Woodley
We say: Cuba 1-0 Trinidad and Tobago
Cuba are likely to try and suffocate Trinidad and Tobago here with their customary deep line, and if they can shut out the Soca Warriors for the first hour or so, we feel they may be able to snatch a winning goal late on.