Cup Winners
| Musim | Kelab | |
| 2023/2024 |  | Inter Miami CF |
| 2022/2023 |  | FC Cincinnati |
| 2021/2022 |  | Los Angeles FC |
| 2020/2021 |  | New England Revolution |
| 2019/2020 |  | Philadelphia Union |
| 2018/2019 | | Los Angeles FC |
| 2017/2018 |  | New York RB |
| 2016/2017 |  | Toronto FC |
| 2015/2016 |  | FC Dallas |
| 2014/2015 | | New York RB |
| 2013/2014 |  | Seattle Sounders |
| 2012/2013 | | New York RB |
| 2011/2012 |  | San Jose Earthquakes |
| 2010/2011 |  | Los Angeles Galaxy |
| 2009/2010 | | Los Angeles Galaxy |
| 2008/2009 |  | Columbus Crew |
| 2007/2008 | | Columbus Crew |
| 2006/2007 |  | D.C. United |
| 2005/2006 | | D.C. United |
| 2004/2005 | | San Jose Earthquakes |
| 2003/2004 | | Columbus Crew |
| 2002/2003 |  | Chicago Fire |
| 2001/2002 | | Los Angeles Galaxy |
| 1999/2000 |  | Sporting KC |
| 1998/1999 | | D.C. United |
| 1997/1998 | | Los Angeles Galaxy |
| 1996/1997 | | D.C. United |