| MLS Cup 1998 | Copa MLS | Chicago Fire |
| MLS Cup 2000 | Copa MLS | Sporting Kansas City |
| MLS Cup 2001 | Copa MLS | San Jose Earthquakes |
| MLS Cup 2002 | Copa MLS | Los Angeles Galaxy |
| MLS Cup 2003 | Copa MLS | San Jose Earthquakes |
| MLS Cup 2006 | Copa MLS | Houston Dynamo |
| MLS Cup 2007 | Copa MLS | Houston Dynamo |
| MLS Cup 2009 | Copa MLS | Real Salt Lake |
| MLS Cup 2020 | Copa MLS | Columbus Crew |
| MLS Cup 2021 | Copa MLS | New York City FC |
| MLS Cup 2022 | Copa MLS | Los Ángeles Football Club |
| MLS Cup 2023 | Copa MLS | Columbus Crew |
| MLS Cup 2024 | Copa MLS | Los Angeles Galaxy |
| MLS Cup 2025 | Copa MLS | Inter de Miami |
| MLS Cup 2026 | Copa MLS | — |