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Treble winners set for a high-stakes reunion

Manchester United Treble winners Dwight Yorke and Steve McClaren are set to manage against each other - with a place in the World Cup finals up for grabs!

Yorke’s Trinidad & Tobago will host McClaren’s Jamaica at the sold-out Hasely Crawford Stadium on Friday (00:00 GMT) as Group H of FIFA’s CONCACAF qualifying stage draws to a close.

Jamaica are top of Group H with nine points from 12 and a win over Trinidad could secure their automatic progression to USA 2026 as pool winners, depending on the result between Dick Advocaat’s Curacao and rock-bottom Bermuda. 

Yorkie's men are third with five points from nine and a win over Jamaica would supercharge their hopes of entering the play-offs as runners-up. 
United legend Dwight Yorke is currently managing Trinidad & Tobago.

THE UNITED FAMILY

Of course, Yorke and McClaren go back a long way. 

Dwight joined United from Aston Villa during the summer of 1998 and McClaren became Alex Ferguson’s assistant in February 1999. Famously, they lifted the Premier League, FA Cup and Champions League at the end of that iconic season. 

Both men left the club in the early 2000s to pursue other projects, but they have remained part of the family, with Yorke working as an ambassador and McClaren returning for a spell as Erik ten Hag’s assistant coach.

Now, their relationship continues as managerial opponents in the Caribbean. 

McClaren's Jamaica had the upper hand in September with a 2-0 home win over Yorke's Trinidad, and it's all to play for in the reverse fixture.

A REMARKABLE JOURNEY

“He was one of the people I reached out to when I was doing my Pro Licence,”
Yorke told The Times. “He helped me go the Asia Cup in Qatar as a technical observer for FIFA alongside himself, Arsene Wenger and Jurgen Klinsmann, which was great learning.

“Our relationship is more than just an ex-player and coach. And here we are, with the rivalry between these countries, battling to qualify for the World Cup. You couldn’t predict that 15, 20 years ago.”
Steve McClaren is hoping to take Jamaica to the 2026 World Cup.
EYES ON SUMMER 2026

Speaking to the press when announcing his latest squad, McClaren was laser focused on achieving automatic qualification for next year’s World Cup finals in North America.

“Jamaicans on this island and all over the world would be so proud if we can achieve this. Everybody's goal was World Cup qualification and we're on the brink. We've had our ups and downs. Successes and failures. Highs and lows. 

“And it all boils down to this. Bedding down our principles and what we have been trying to do. What we want and expect from each other. These games are all about attitude, fight and will to win.”

The Treble season: