Under the tutelage of former international player, 39 year old Everald Cummings, Trinidad&Tobago set out to impose themselves on the CONCACAF World Cup qualification scene, which on their part started in April 1988. 

We have no information of any friendlies played prior to the start of the World Cup and CONCACAF championships qualifiers, They were up against Guyana in the first qualifying round, a team they had beaten 2-1 away in a friendly in September the previous year. 

First qualifying round: 

17/4-1988: Guyana 0-4 Trinidad&Tobago
Goals: Elliott-Allen (41), Faustin (71), Lake (77), Skeene (85)
Line-up: Maurice – Williams, C Morris, Francis, Faustin – Charles, Waterman (M Morris 63), Skeene, Lewis – Elliott-Allen, Jones (Jamerson 73)

8/5-1988: Trinidad&Tobago 1-0 Guyana
Goal: Corneal (68)
Line-up: Lovell – Williams, C Morris, Francis, Faustin – Charles, La Forest (Corneal 53), Skeene (Jamerson 62), Lewis – Elliott-Allen, Jones

Trinidad&Tobago progress through to the next round with a 5-0 aggregate score.

Second qualifying round: 

30/10-1988: Trinidad&Tobago 0-0 Honduras 
Line-up: Maurice – Williams, C Morris, Francis, Faustin – Charles, Skeene (Jamerson 34), Lawrence, Latapy, Chinapoo – Corneal (Jones 52)

13/11-1988: Honduras 1-1 Trinidad&Tobago
Goal: Charles (56)
Line-up: Maurice – Williams, C Morris, Francis, Faustin – Charles, Skeene, Lawrence, Latapy, Chinapoo – Corneal

Trinidad&Tobago progress through to the qualification group stage, which doubles as the CONCACAF championship, on the away goals rule following a 1-1 aggregate score.

Qualification group stage: 

Match 1
13/5-1989: USA 1-1 Trinidad&Tobago
Goal: Charles (88)
Line-up (4-5-1): Carter – Williams, C Morris, Francis, Faustin – Charles, Elliott-Allen (Jamerson 62), Lawrence, Latapy, Lewis – Alibey (M Morris 69)

Match 2
28/5-1989: Trinidad&Tobago 1-1 Costa Rica
Goal: Jones (68)
Line-up: Carter – Williams, C Morris, Francis, Faustin – M Morris (Nelson 55), Charles, Lawrence, Latapy (Jones h-t), Lewis – Alibey

Match 3
11/6-1989: Costa Rica 1-0 Trinidad&Tobago
Line-up: Carter – Williams, C Morris (c), Francis, Faustin – Skeene (Lewis 59), Yorke, Jamerson, Chinapoo (Latapy 71), Charles – Alibey

Match 4
30/7-1989: Trinidad&Tobago 2-0 El Salvador
Goals: Lewis (50, 61)
Line-up: Maurice – Williams, C Morris, Francis, Faustin – Charles, Jamerson, Latapy, Lewis – Yorke (Lee 83), Jones

Match 5
13/8-1989: El Salvador 0-0 Trinidad&Tobago
Line-up: Maurice – Williams, C Morris, Francis, Faustin – Charles, Jamerson (Elliott-Allen 70), Latapy, Lewis – Yorke (M Morris 69), Jones

Match 6
20/8-1989: Guatemala 0-1 Trinidad&Tobago
Goal: Jamerson (57)
Line-up (4-5-1): Maurice – Williams, C Morris (c), Francis, Faustin – Alibey (M Morris 80), Charles (Yorke h-t), Jamerson, Latapy, Lewis – Jones

Match 7
3/9-1989: Trinidad&Tobago 2-1 Guatemala
Goals: Jones (11), Jamerson (88)
Line-up (4-3-3): Maurice – Lee, C Morris (c), Francis, Faustin – Charles, Jamerson, Latapy – Yorke (M Morris 67), Jones (Alibey 75), Lewis

Match 8
19/11-1989: Trinidad&Tobago 0-1 USA 
Line-up (4-3-3): Maurice – Williams, C Morris (c), Francis, Faustin – Latapy, Jamerson, Elliott-Allen (Alibey 75) – Yorke (Charles 60), Jones, Lewis
Having waited for more than two and a half months for their final push to try and reach a World Cup for the very first time, Trinidad&Tobago disappointed those who had packed the stadium to come and cheer them on. They looked a bit wobbly from the off, and never settled or started playing some of the football which they’d shown throughout the qualification campaign. They conceded after half an hour, and it always looked an uphill battle from then on, as the hosts never found an answer to the tight defending and strict organization from the US team. Key performers had an off-day, most notably Latapy and Yorke. 

Qualification verdict

Surely, Trinidad&Tobago had been rank outsiders by the start of the qualification group stage, even if they had got to that stage by defeating a Honduran outfit which still had some remnants left from the team which had competed at the 1982 World Cup in Spain. 

Manager Everald Cummings had built a solid unit with keen, young players, and they were well organized in the final third of the pitch, while they would often rely on individual skills going forward. They had in Russell Latapy a gifted playmaker, and 20 years by the start of the qualification group stage, he accepted his responsibility as a key performer, often leading quick transitions from defence to attack. Another vital performer was left-sided man Leonson Lewis. He notched both goals in their 2-0 home win against El Salvador, their first win in the match which saw them develop belief that they could challenge for a place at Italia ’90. 

The longer the qualification ran, the better the results for the Trinis team, as they gained seven from a possible eight points in successive double headers against El Salvador and Guatemala. A player who was turning into a key performer was holding midfield man Kerry Jamerson. The 22 year old was not only impressively built physically, but he both shielded his centre-backs from the base of the midfield, and scored two match winning goals in the games against Guatemala, who had participated at the Olympic Games football tournament a year earlier. Jamerson’s long strides became a familiar sight. Behind him, the highly dependable centre-back pairing of captain Clayton Morris and the strapping Dexter Francis was an equally impressive and important feature in their set-up. 

Trinidad&Tobago had needed to wait for more than two and a half months before their final, decisive qualifier at home to USA, and coming into that game, in a festival draped, carnival clad national stadium in the capital Port of Spain, they somehow seemed drained, unable to capitalize on the vibe and the energy from the 35,000 strong crowd. Young forward Dwight Yorke had recently signed for English giants Aston Villa, and was another one who had impressed with his mature displays, often from the wide right role in Cummings’ 4-3-3 formation. Having turned 18 only for their final qualifier, the starled ultimately failed to deliver, and was substituted on the hour. He wasn’t alone. Latapy was another who failed to live up to his billing when it mattered the most, while the same, too, could be said for striker Philibert Jones, who was their third player to have notched twice during the course of the group stage qualification. 

There was no reason to point blame to any one individual. Trinidad&Tobago had done so well to put themselves in the frame for qualification before the last game, and among a youthful line-up, they had so much going for them, with every chance to improve as a unit and challenge again for the next World Cup qualification.