On Tuesday, Mexico will once again return to Port of Spain as they continue their Hexagonal campaign with their third road game after the first four matches.
Mexico has had a long and interesting history against Trinidad and Tobago. Trinidad and Tobago was the home of Jack Warner, who for years was the head of CONCACAF and became a huge figure within the federation. This, of course, led to lots of "interesting" things and Mexico was at the center of many of them.
The first match in a World Cup qualifier between Mexico and Trinidad and Tobago in the Caribbean was also the most infamous. In 1973, Trinidad and Tobago crushed Mexico 4-0 and eliminated them from the 1974 World Cup. This is still one of the worst defeats in Mexico's history and one of the darkest pages in Mexican football. The notable thing was that, although it was in the Caribbean, it didn't happen in Trinidad but in Haiti, where the qualifiers were being held tournament style. The defeat had historic significant and stood alone for years, as Mexico never played Trinidad in a World Cup qualifier until the next century.
In 2000, Mexico finally played a World Cup qualifier in Port of Spain and also had another controversial defeat. While Mexico had played and beaten Trinidad and Tobago in Trinidad before, the first qualifier resulted in a shock 1-0 win for Trinidad and Tobago and it severely hurt Manuel Lapuente's tenure. Lapuente had some bad results in the year 2000 and was facing strong criticism from then Toluca general manager Rafael Lebrija and some other soccer executives. The relationship had arrived to the point that after Mexico won their next two games against Canada and Panama to qualify to the Hexagonal round, Lapuente quit. Toluca coach Enrique Meza came in and in a weird coincidence crushed Trinidad and Tobago in his first WC qualifier in Mexico City, but El Tri suffered a devastating injury to Cuauhtemoc Blanco that help doomed what would be one of the worst tenures ever in NT history, if not the worst.
In 2001 and right in the middle of the terrible storm that was Enrique Meza's tenure, Mexico went to Trinidad and Tobago in the hexagonal and got a 1-1 draw. After going down, Mexico tied in the second half off a great long range goal by Pavel Pardo. Mexico had a couple of chances that they wasted and would eventually haunt Mexico: El Tri would go on to have the Aztecazo against Costa Rica in their next qualifier and then lose badly to Honduras, putting them on the brink of elimination.
In 2004 Mexico would face Trinidad and Tobago again, this time in the semifinal group. In a group that looked suspiciously easy for Jack Warner's team, Mexico and T&T were joined by Caribbean teams St Vincent and the Grenadines and St. Kitts and Nevis. By that logic, Mexico’s toughest game of the round would be the away game to T&Y, which they won easily 3-1 with two goals by Jesus Arellano and another one by Jared Borgetti. Trinidad's goal by Stern John would be the only goal scored on Mexico in the semifinal round.
In 2005 Mexico would once again face Trinidad and Tobago in what might be the most controversial game of all. Mexico lost 2-1 against Trinidad in the final game of the Hexagonal. Mexico had already qualified to the World Cup, while Trinidad and Tobago had a two point lead over Guatemala for the playoff spot against the AFC team. The win clinched the spot for Trinidad.
Years later, Ricardo La Volpe would say in an interview that Mexico didn't want any problems with Warner, implying that Mexico might have not gone full out against Trinidad and Tobago and tanked the game for them. The comments brought lot of controversy, especially from the side of Guatemala fans that had thought for years something was off about that result (something that is still felt to this day by many).
The last meeting in a WC qualifiers in Trinidad and Tobago happened in 2009. Once again it was the final game of the Hexagonal, but this time Trinidad and Tobago was already eliminated and out of the World Cup. Mexico had qualified in the game before against El Salvador. The only thing in play was the meaningless top of the Hex crown and Mexico tied 2-2 in a game that many players said they didn’t care for.