Steve McClaren’s journey as the head coach of Jamaica’s national football team came to an abrupt and disappointing end following the Reggae Boyz’s failure to secure a spot in the 2026 FIFA World Cup. McClaren, who took charge in July 2024, faced significant challenges throughout his 475-day tenure, which concluded with a 0-0 draw against Curacao in Kingston on November 18, 2025. This result left Jamaica out of automatic qualification, forcing them into a last-chance inter-confederation playoff in March 2026. McClaren’s resignation, announced during his final press conference, marked the culmination of a turbulent period marked by fan discontent, internal friction, and unmet expectations. His decision to remain in England rather than relocate to Jamaica, his perceived bias towards England-born players, and the team’s underwhelming performances in key tournaments contributed to his downfall. Despite initial optimism and support from the Jamaica Football Federation (JFF), McClaren’s inability to deliver results ultimately sealed his fate. The Reggae Boyz now face an uphill battle to qualify for the World Cup under interim coach Rudolph Speid, while McClaren’s future in international football remains uncertain.