Jamaica vs Trinidad and Tobago Preview & Prediction
The upcoming friendly between Jamaica and Trinidad and Tobago promises to be a closely contested affair as both teams continue their preparations ahead of competitive fixtures. Jamaica enters this match in solid form, having secured a convincing 3-0 victory over St. Vincent and the Grenadines in their recent CONCACAF Gold Cup qualification game and remaining unbeaten in their last five matches. Trinidad and Tobago, meanwhile, have also shown strength, particularly in their home qualifiers where they recorded a dominant 4-0 win against Cuba. This Friendlies match preview highlights the intriguing dynamics between two Caribbean rivals striving to assert their dominance.
Under the guidance of coach McClaren, Jamaica has demonstrated a balanced tactical approach, blending defensive solidity with effective attacking transitions. Their recent performances reveal a team that is difficult to break down, as evidenced by their clean sheet against St. Vincent and the Grenadines and a narrow 1-0 win over Trinidad and Tobago earlier this year. Jamaica’s recent form suggests a disciplined side capable of controlling the midfield and capitalizing on key moments, which bodes well for their home performance. McClaren’s emphasis on structure and resilience has been a defining feature of Jamaica’s gameplay, making them a formidable opponent in this fixture.
Trinidad and Tobago, coached by Yorke, have shown a positive form guide, especially in their Gold Cup qualifiers where they secured back-to-back victories against Cuba. Their away performance, however, has been more mixed, with a recent 1-1 draw against Jamaica and a loss to the USA highlighting some vulnerabilities on the road. Yorke’s tactical setup often focuses on quick counter-attacks and exploiting spaces behind the defense, but maintaining defensive discipline remains a challenge for the visitors. Despite these weaknesses, Trinidad and Tobago’s attacking prowess was on full display during their 4-0 win, signaling their capability to score and pressure opponents when in form.
Looking at the Jamaica vs Trinidad and Tobago head to head record, recent encounters have been tightly contested. Over the last five finished matches, Jamaica holds a slight edge with three wins, including a commanding 4-1 victory in June 2023 and a narrow 1-0 win in March 2024. Trinidad and Tobago have managed to secure a hard-fought 1-1 draw in their latest meeting, demonstrating their resilience. The series of low-scoring matches and draws, including a 0-0 stalemate in March 2024, highlight the competitive nature and tactical caution both teams employ against each other.
Given the tactical analysis and recent form of both sides, the Jamaica vs Trinidad and Tobago prediction leans towards an under 3.5 goals outcome. Both teams have shown strong defensive organization and have kept matches tight historically, suggesting that this friendly will likely be a strategic battle rather than a high-scoring spectacle. For those wondering who will win Jamaica vs Trinidad and Tobago, the home advantage and slightly superior recent results may tip the scale in favor of Jamaica, but expect a closely fought contest. Betting tips would advise caution on expecting a goal-fest and instead focus on disciplined play and potential narrow margins.
A hot stat to note: Jamaica has not conceded more than one goal in any of their last five encounters against Trinidad and Tobago, underscoring their defensive resilience in this rivalry. This fact further supports the prediction of an under 3.5 goals match and adds an interesting angle to this exciting Friendlies match preview.
Jamaica vs Trinidad and Tobago Prediction
Match: Jamaica vs Trinidad and Tobago
Kick Off: 27 May 2025, 18:00 UTC
Prediction: Under 3.5

Jamaica
vs

Trinidad and Tobago
Jamaica vs Trinidad and Tobago – Friendlies Standings
Standings data not available for Friendlies (2025).
Jamaica vs Trinidad and Tobago Head-to-Head
Date | League | Match | Score |
---|---|---|---|
27 May 2025 | Friendlies |
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– – – |
10 Feb 2025 | Friendlies |
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1 – 1 |
07 Feb 2025 | Friendlies |
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1 – 0 |
03 Mar 2024 | Friendlies |
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0 – 0 |
01 Mar 2024 | Friendlies |
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0 – 1 |
28 Jun 2023 | CONCACAF Gold Cup |
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4 – 1 |
15 Mar 2023 | Friendlies |
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0 – 0 |
11 Mar 2023 | Friendlies |
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0 – 1 |
25 Aug 2017 | Friendlies |
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1 – 2 |
19 Nov 2014 | Caribbean Cup |
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0 – 0 |