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