| Kausi | Voittaja | Tulos[2] | Häviäjä | Stadion | Kaupunki | Yleisö |
| 1996 | D.C. United | 3–2 ja | Los Angeles Galaxy | Foxboro Stadium | Foxborough, Massachusetts | 34 643 |
| 1997 | D.C. United | 2–1 | Colorado Rapids | RFK Stadium | Washington | 57 431 |
| 1998 | Chicago Fire | 2–0 | D.C. United | Rose Bowl | Pasadena, Kalifornia | 51 350 |
| 1999 | D.C. United | 2–0 | Los Angeles Galaxy | Foxboro Stadium | Foxborough, Massachusetts | 44 910 |
| 2000 | Kansas City Wizards | 1–0 | Chicago Fire | RFK Stadium | Washington | 39 159 |
| 2001 | San Jose Earthquakes | 2–1 ja | Los Angeles Galaxy | Columbus Crew Stadium | Columbus, Ohio | 21 626 |
| 2002 | Los Angeles Galaxy | 1–0 ja | New England Revolution | Gillette Stadium | Foxborough, Massachusetts | 61 316 |
| 2003 | San Jose Earthquakes | 4–2 | Chicago Fire | The Home Depot Center | Carson, Kalifornia | 22 000 |
| 2004 | D.C. United | 3–2 | Kansas City Wizards | The Home Depot Center | Carson, Kalifornia | 22 000 |
| 2005 | Los Angeles Galaxy | 1–0 ja | New England Revolution | Pizza Hut Park | Frisco, Texas | 21 193 |
| 2006 | Houston Dynamo | 1–1 (4–3 rp) | New England Revolution | Pizza Hut Park | Frisco, Texas | 22 427 |
| 2007 | Houston Dynamo | 2–1 | New England Revolution | RFK Stadium | Washington | 39 859 |
| 2008 | Columbus Crew | 3–1 | New York Red Bulls | The Home Depot Center | Carson, Kalifornia | 27 000 |
| 2009 | Real Salt Lake | 1–1 (5–4 rp) | Los Angeles Galaxy | Qwest Field | Seattle, Washington | 46 011 |
| 2010 | Colorado Rapids | 2–1 ja | FC Dallas | BMO Field | Toronto, Ontario | 21 700 |
| 2011 | Los Angeles Galaxy | 1–0 | Houston Dynamo | The Home Depot Center | Carson, Kalifornia | 30 281 |
| 2012 | Los Angeles Galaxy | 3–1 | Houston Dynamo | The Home Depot Center | Carson, Kalifornia | 30 510 |
| 2013 | Sporting Kansas City | 1–1 (7–6 rp) | Real Salt Lake | Sporting Park | Kansas City, Kansas | 21 650 |
| 2014 | Los Angeles Galaxy | 2–1 ja | New England Revolution | StubHub Center | Carson, Kalifornia | 27 000 |
| 2015 | Portland Timbers | 2–1 | Columbus Crew | Mapfre Stadium | Columbus, Ohio | 21 747 |
| 2016 | Seattle Sounders FC | 0–0 (5–4 rp) | Toronto FC | BMO Field | Toronto, Ontario | 36 045 |
| 2017 | Toronto FC | 2–0 | Seattle Sounders FC | BMO Field | Toronto, Ontario | 30 584 |
| 2018 | Atlanta United FC | 2–0 | Portland Timbers | Mercedes-Benz Stadium | Atlanta, Georgia ] | 73 019 |
| 2019 | Seattle Sounders FC | 3–1 | Seattle Sounders FC | CentruyLink Field | Seattle, Washington | 69 274 |
| 2020 | Columbus Crew | 3–0 | Seattle Sounders FC | Mapfre Stadium | Columbus, Ohio | 1 500^ |
| 2021 | New York City FC | 1–1 (4–2 rp) | Portland Timbers | Providence Park | Portland, Oregon | 25 218 |
| 2022 | Los Angeles FC | 3–3 (3–0 rp) | Philadelphia Union | Banc of California Stadium | Los Angeles, Kalifornia | 22 384 |
| 2023 | Columbus Crew | 2–1 | Los Angeles FC | Lower.com Field | Columbus, Ohio | 20 802 |
| 2024 | Los Angeles Galaxy | 2–1 | New York Red Bulls | Dignity Health Sports Park | Carson, Kalifornia | 26 812 |
| 2025 | Inter Miami CF | 3–1 | Vancouver Whitecaps FC | Chase Stadium | Fort Lauderdale, Florida | 21 556 |
^ Osallistuminen vuonna 2020 oli rajoitettu COVID-19:n vuoksi.
Kanadalainen Dwayne De Rosario on valittu kahdesti MLS Cupin arvokkaimmaksi pelaajaksi.