Cup Winners
| Sezon | Kulüp | |
| 2023/2024 |  | Los Angeles FC |
| 2022/2023 |  | Houston Dynamo |
| 2021/2022 |  | Orlando City SC |
| 2018/2019 |  | Atlanta United |
| 2013/2014 |  | Seattle Sounders |
| 2012/2013 |  | D.C. United |
| 2011/2012 |  | Sporting KC |
| 2010/2011 | | Seattle Sounders |
| 2009/2010 | | Seattle Sounders |
| 2008/2009 | | Seattle Sounders |
| 2007/2008 | | D.C. United |
| 2006/2007 |  | New England Revolution |
| 2005/2006 |  | Chicago Fire |
| 2004/2005 |  | Los Angeles Galaxy |
| 2003/2004 | | Sporting KC |
| 2002/2003 | | Chicago Fire |
| 2001/2002 |  | Columbus Crew |
| 2000/2001 | | Los Angeles Galaxy |
| 1999/2000 | | Chicago Fire |
| 1998/1999 |  | Rochester Rhinos |
| 1997/1998 | | Chicago Fire |
| 1996/1997 |  | FC Dallas |
| 1995/1996 | | D.C. United |
| 1994/1995 |  | Richmond Kickers |