The list of MLS Cup winning head coaches includes six 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 and Caleb Porter, who have each won MLS Cup twice. To date, three 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) and Caleb Porter (with Portland Timbers in 2015 and Columbus Crew in 2020).
