St. Lucia

Third place at the 1991 Caribbean Cup remains the high point for The Piton Boyz, and it was earned rather than gifted: four wins and two draws across the group stage before Saint Lucia's footballers had ever played a World Cup qualifier of note. Twenty-three years passed before another trophy followed, and that one came at their neighbours' expense — the Windward Islands Tournament in 2014, sealed with a 2–0 win over Dominica and a 1–0 win over Grenada.

Dominica has been the closest thing to a fixed point on the calendar since. Eighteen meetings by 2023, eleven of them won by Saint Lucia, have made it the match that keeps coming back round on the draw more than any other, even without a name attached to it. The team's most startling result, though, came against Aruba in 2014 World Cup qualifying: a 4–2 defeat away from home looked to have ended the tie until the return leg produced the same 4–2 scoreline after extra time, and Saint Lucia went through on penalties, 5–4.

The nickname predates none of that — it comes from the twin volcanic peaks of the Pitons rather than from anything won on a pitch — and the Saint Lucia Football Association that runs the side was formed in 1979, the year the island became independent. Stern John, who had played in the Premier League for West Ham and Birmingham, took charge in 2022 and left in 2026 with 12 wins from 25 games, a record that nudged the team up the rankings without changing what it had already done in 1991.

Kurt Frederick has worn the captain's armband since 2010 and holds the appearance record outright, 69 caps and counting, but it is Earl Jean's name that still stands above the scoring charts — 20 goals from just 23 caps between 1990 and 2004, a return no one since has come close to matching.