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| 1 MLS Cup championship season: 1998 |
| Last MLS Cup championship: 1998, 24 seasons ago |
| Best finish: |
| beat DC United in MLS Cup Finals in 1998 |
| TEAM | SEASON | RECORD | PTS | DIV STAND | PLAYOFFS |
| %Chicago | 1998 | 20-12 | 56 pts | 2nd West Conf | WCol WLA WDC |
| Chicago | 1999 | 18-14 | 48 pts | 3rd West Conf | LDBu |
| Chicago | 2000 | 17-9-6 | 57 pts | 1st Cent Div | WNE WMet LKCW |
| Chicago | 2001 | 16-6-5 | 53 pts | 1st Cent Div | WDBu LLA |
| Chicago | 2002 | 11-13-4 | 37 pts | 3rd East Conf | LNE |
| Chicago | 2003 | 15-7-8 | 53 pts | 1st East Conf | WKC WNE LSJ |
| Chicago | 2004 | 8-13-9 | 33 pts | 5th East Conf | missed playoffs |
| Chicago | 2005 | 15-13-4 | 49 pts | 3rd East Conf | WDC LNE |
| Chicago | 2006 | 13-11-8 | 47 pts | 3rd East Conf | LChi |
| Chicago | 2007 | 10-10-10 | 40 pts | 4th East Conf | WDC LNE |
| Chicago | 2008 | 13-10-7 | 46 pts | 2nd East Conf | WNE LCbs |
| Chicago | 2009 | 11-7-12 | 45 pts | 2nd East Conf | WNE LRSL |
| Chicago | 2010 | 9-12-9 | 36 pts | 4th East Conf | missed playoffs |
| Chicago | 2011 | 9-9-16 | 43 pts | 6th East Conf | missed playoffs |
| Chicago | 2012 | 17-11-6 | 57 pts | 4th East Conf | LHou |
| Chicago | 2013 | 14-13-7 | 48 pts | 6th East Conf | missed playoffs |
| Chicago | 2014 | 6-10-18 | 36 pts | 9th East Conf | missed playoffs |
| Chicago | 2015 | 8-20-6 | 30 pts | 10th East Conf | missed playoffs |
| Chicago | 2016 | 7-17-10 | 31 pts | 10th East Conf | missed playoffs |
| Chicago | 2017 | 16-11-7 | 55 pts | 3rd East Conf | LNYR |
| Chicago | 2018 | 8-18-8 | 32 pts | 10th East Conf | missed playoffs |
| Chicago | 2019 | 10-12-12 | 42 pts | 8th East Conf | missed playoffs |
| Chicago | 2020 | 5-10-8 | 23 pts | 11th East Conf | missed playoffs |
| Chicago | 2021 | 9-18-7 | 34 pts | 12th East Conf | missed playoffs |