List of MLS Cup winning head coaches
The list of MLS Cup winning head coaches includes seven head coaches who have won multiple MLS Cup titles — Bruce Arena, who has won MLS Cup five times, and Sigi Schmid, Frank Yallop, Dominic Kinnear, Brian Schmetzer, Caleb Porter and Greg Vanney, who have each won MLS Cup twice.
To date, four head coaches have led two different clubs to win the MLS Cup: Sigi Schmid, Bruce Arena, Caleb Porter and Greg Vanney.
Only two head coaches have won the playoffs as both a player and head coach. Piotr Nowak played for Chicago Fire during their 1998 MLS Cup title, and subsequently led D.C. United as a coach to their fourth MLS Cup title in 2004. Peter Vermes won the 2000 MLS Cup with Sporting Kansas City as a player, then won MLS Cup with the same team as a coach in 2013. The next closest head coaches to such an achievement are Dominic Kinnear and Greg Vanney. Kinnear was on the Colorado Rapids squad that lost the 1997 MLS Cup final; however, he led the Houston Dynamo to two straight MLS Cup titles in 2006 and 2007. Vanney was on the LA Galaxy roster that finished as runners-up in 1996 and 2001, and coached Toronto FC and the LA Galaxy to victory in 2017 and 2024, respectively.
Wilfried Nancy led the Columbus Crew to an MLS Cup victory in 2023 and became the first Black manager of a cup-winning team.
Winning head coaches
| Final | Winning head coach | Nationality | Club | |||||||||||||||||||||||||||||||
| 1996 |  United Statessortname|Bruce|ArenaCoaches with multiple MLS Cup victories
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