To date, four head coaches have led two different clubs to win the MLS Cup: Sigi Schmid (with Los Angeles Galaxy in 2002 and Columbus Crew in 2008), Bruce Arena (with D.C. United in 1996 and 1997 and LA Galaxy in 2011, 2012 and 2014), Caleb Porter (with Portland Timbers in 2015 and Columbus Crew in 2020) and Greg Vanney (with Toronto FC in 2017 and LA Galaxy in 2024).
Piotr Nowak played for Chicago Fire during their 1998 MLS Cup title (in which he was named the Man of the Match), 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 (then known as the Kansas City Wizards) 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.
Wilfried Nancy led the Columbus Crew to an MLS Cup victory in 2023 and became the first Black manager of a cup-winning team.