O’Shea, Dinwiddie set to square off in second Grey Cup showdown as CFL head coaches

Mike O’Shea and Ryan Dinwiddie are together again at the Grey Cup.

Winnipeg faces Toronto in the CFL championship game Sunday at B.C. Place Stadium, the second meeting in three years between the two teams after the Argonauts edged the Blue Bombers 24-23 in the 2022 game.

Winnipeg is making its fifth straight Grey Cup appearance under O’Shea and chasing a third victory.

Dinwiddie is completing his fourth season with Toronto, having led the franchise to three straight first-place finishes in the East Division before ending up second spot in 2024.

Both head coaches have made previous Grey Cup appearances as players and assistant coaches.

After winning three Grey Cups as a player with Toronto (1996-97, ’04), O’Shea earned a fourth championship ring with the Argos as their special-teams co-ordinator in 2012.

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Dinwiddie made his first career CFL start as a quarterback with Winnipeg in the 2007 Grey Cup, but the Bombers lost 23-19 to Saskatchewan.

But Dinwiddie earned a ring in 2018 as Calgary’s quarterback coach.