| MLS Cup 1996 | D.C. United |
| MLS Cup 1997 | D.C. United |
| MLS Cup 1998 | Chicago Fire FC |
| MLS Cup 1999 | D.C. United |
| MLS Cup 2000 | Sporting Kansas City |
| MLS Cup 2001 | San Jose Earthquakes |
| MLS Cup 2002 | Los Angeles Galaxy |
| MLS Cup 2003 | San Jose Earthquakes |
| MLS Cup 2004 | D.C. United |
| MLS Cup 2005 | Los Angeles Galaxy |
| MLS Cup 2006 | Houston Dynamo |
| MLS Cup 2007 | Houston Dynamo |
| MLS Cup 2008 | Columbus Crew |
| MLS Cup 2009 | Real Salt Lake |
| MLS Cup 2010 | FC Dallas |
| MLS Cup 2011 | Los Angeles Galaxy |
| MLS Cup 2012 | Los Angeles Galaxy |
| MLS Cup 2013 | Sporting Kansas City |
| MLS Cup 2014 | Los Angeles Galaxy |
| MLS Cup 2015 | Portland Timbers |
| MLS Cup 2016 | Toronto FC |
| MLS Cup 2017 | Toronto FC |
| MLS Cup 2018 | Atlanta United FC |
| MLS Cup 2019 | Seattle Sounders FC |
| MLS Cup 2020 | Columbus Crew |
| MLS Cup 2021 | New York City FC |
| MLS Cup 2022 | Los Angeles Football Club |
| MLS Cup 2023 | Columbus Crew |
| MLS Cup 2024 | Los Angeles Galaxy |
| MLS Cup 2025 | Club Internacional de Fútbol Miami |
| MLS Cup 2026 | — |