The regional powers have met in the competition's championship match once before. In 1999, the host Soca Warriors prevailed 2-1 on an extra-time goal by Stern John at Hasely Crawford Stadium in Port of Spain.
More recently, they squared off last month in the qualifying stage at Dwight Yorke Stadium in Bacolet, Tobago. Trinidad, once again, emerged as the winner, 1-0. Ataullah Guerra netted the 67th minute winner, giving his team a first-place finish in Group 8.
Trinidad started the finals slowly, drawing with Haiti (0-0) and losing to Antigua (2-0). But a 2-1 win over the Dominican Republic sealed a semifinal place and a berth in the 2013 CONCACAF Gold Cup. The Soca Warriors advanced to the championship match by getting past Martinique 5-4 on penalties after a 1-1 draw.
Though momentum has built as the tournament progressed, team captain Jan Michael Williams admitted the Soca Warriors did not play well early on, but they have improved. He is optimistic, though cautious, about encountering the Lions of the Caribbean.
"We know the Cuban team, of course, and we watched them during the semis as they beat Haiti, so we have a good idea of what to expect," said the towering DirecTV W Connection goalkeeper. "We know where we want to attack and who are their key players, who we have to shut down, so I'm expecting a fun but victorious final for Trinidad."
Trinidad's main attack will come from the feet of Guerra, a bright spot all tournament. He has created numerous chances, showing an impressive ability to find the open man, as well as to pull the trigger himself.
Kevin Molino provides instant energy and was used off the bench in the semifinal against Martinique, set-up Richard Roy for the late equalizer. The midfielder, 22, is expected to be in the starting eleven against Cuba.
Additionally, if successful, Trinidad will be the first side to win the Caribbean Cup with co-head coaches, as the duo of Hutson Charles and Jamaal Shabazz manage the squad in tandem.
"We had specific goals and our first one coming here was to qualify for the Gold Cup and we did that, then our second goal was to reach the final and that has been accomplished," said Shabazz, who was Guyana's head coach through the semifinal round of CONCACAF World Cup Qualifying for Brazil 2014. "Now we have a strong desire to become Caribbean champions."
For Cuba's part, it will rely on midfield general Alberto Gomez. The 24-year-old has been nothing short of brilliant and one of the tournament's revelations. Trinidad will have to account for his speed and ability to take-on defenders.
Gomez will be looking to provide service to Marcel Hernandez and Ariel Martinez. The forwards have combined to score seven goals in qualifying and the finals.
Two talented teams with outstanding players will hope to lift the trophy. Only one thing is certain, by Sunday evening, there will be a new champion of Caribbean football.