| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 26 | Sat 9/6 9:00am | 8U-7V7/5S | CHICAGO EMPIRE FC SOUTH 18/19 GOLD vs CHICAGO UNITED 2018 WARRIORS | 33 | CAESAR PARK | 4v4, 7v7, 9v9 |
| 615 | Sat 9/6 2:00pm | 9U/5S | LEGACY SC 2017 vs CHICAGO UNITED 2017 STORM | 26 | SPENCER SCHOOL CAMPUS | Field 12 - 7v7 |
| 743 | Sat 9/6 3:15pm | 10U/5SE | ACADEMIA ATLAS FC 2016 BLACK vs CHICAGO UNITED 2016 FALCONS | 32 | VITTUM PARK | 7V7 |
| 274* | Sun 9/7 11:15am |
12U/5S | CHICAGO KICS 2014 BLUE (SOUTH) vs CHICAGO UNITED 2014 LEGENDS | 25 | EVERGREEN PARK HIGH SCHOOL | 9v9 |
| 1045 | Sat 9/13 10:00am | 12U/5S | CHICAGO UNITED 2014 LEGENDS vs LEGACY SC 2014 SELECT | 33 | ALTMAN PARK | 9v9 |
| 1366 | Sat 9/13 1:00pm | 9U/5S | CHICAGO UNITED 2017 STORM vs ORLAND PARK STING FC 2017 ELITE | 33 | ALTMAN PARK | 7v7 |
| 1521 | Sat 9/13 2:30pm | 8U-7V7/5S | CHICAGO UNITED 2018 WARRIORS vs LTSC 2018/19 TRAVEL WHITE | 33 | ALTMAN PARK | 7v7 |
| 1228* | Sat 9/13 3:30pm | 10U/5SE | CHICAGO UNITED 2016 FALCONS vs RANGERS SOCCER ACADEMY 2016 | 33 | CHIEF MIKE O'CONNELL PARK | |
| 1365 | Sun 9/14 1:00pm | 15U-FS/5S | CHICAGO BLAST 2011 RED vs CHICAGO UNITED 2011 EAGLES | 17 | OAK BROOK PARK DISTRICT | |
| 1547 | Sun 9/14 3:00pm | 13U/5SE | CHICAGO UNITED 2013 TITANS vs ORLAND PARK STING FC 2013 SELECT 2 | 33 | ALTMAN PARK | 11v11 |
| 5691* | Mon 9/15 6:00pm | 9U/5S | CHICAGO UNITED 2017 STORM vs WINDY CITY PRIDE 2017 | 33 | COMMUNITY PARK (TINLEY PARK) | |
| 1771 | Sat 9/20 9:00am | 8U-7V7/5S | CHICAGO EMPIRE FC 2018 BLUE 1 vs CHICAGO UNITED 2018 WARRIORS | 17 | OAK BROOK POLO FIELDS | J 7v7 |
| 1906 | Sat 9/20 10:00am | 12U/5S | CHICAGO UNITED 2014 LEGENDS vs MT GREENWOOD KNIGHTS SC 14 | 33 | ALTMAN PARK | 9v9 |
| 2078 | Sat 9/20 11:30am | 10U/5SE | CHICAGO UNITED 2016 FALCONS vs MT GREENWOOD KNIGHTS SC 16 | 33 | ALTMAN PARK | 7v7 |
| 2181* | Sat 9/20 12:00pm | 13U/5SE | MUSTANGS UNITED FC 2013 vs CHICAGO UNITED 2013 TITANS | 17 | FITZGERALD PARK | |
| 2243* | Sun 9/21 2:00pm |
15U-FS/5S | CHICAGO UNITED 2011 EAGLES vs MIDWEST ELITE SC 2011 | 33 | FREEDOM FIELD (TINLEY PARK) | |
| 5182* | Sun 9/21 3:00pm | 13U/5SE | ACADEMIA ATLAS 2013/14 RED vs CHICAGO UNITED 2013 TITANS | 32 | SUMMIT PARK (SUMMIT) | |
| 5786* | Sun 9/21 4:00pm |
12U/5S | UESC - CHICAGOLAND 2014 SEL WHITE BB vs CHICAGO UNITED 2014 LEGENDS | 33 | DYNAMO FIELD | 9v9 |
| 487* | Sat 9/27 10:00am | 15U-FS/5S | CHICAGO UNITED 2011 EAGLES vs KORA FC 2011 ELITE | 33 | FREEDOM FIELD (TINLEY PARK) | |
| 2921 | Sat 9/27 11:00am | 10U/5SE | EU FURY FC 2016 vs CHICAGO UNITED 2016 FALCONS | 17 | DURKIN PARK | |
| 3048* | Sun 9/28 12:00pm | 9U/5S | MUSTANGS UNITED FC 2017 vs CHICAGO UNITED 2017 STORM | 17 | MARTIN PARK | |
| 3114 | Sun 9/28 1:00pm | 15U-FS/5S | CHICAGO UNITED 2011 EAGLES vs CFA - MIDWEST WINGS 2011/12 | 33 | ALTMAN PARK | 11v11 |
| 3271* | Sun 9/28 2:30pm | 8U-7V7/5S | CHICAGO UNITED 2018 WARRIORS vs RUSH OSWEGO 2018 PREMIER | 33 | CHIEF MIKE O'CONNELL PARK | |
| 2775* | Sun 9/28 3:00pm | 12U/5S | CHICAGO UNITED 2014 LEGENDS vs YOUNG WOLVES 2014 | 33 | FREEDOM FIELD (TINLEY PARK) | |
| 6753* | Sun 9/28 5:00pm | 13U/5SE | CHICAGO UNITED 2013 TITANS vs CRESTWOOD SC 2013/14 | 33 | FREEDOM FIELD (TINLEY PARK) | |
| 3613 | Sat 10/4 9:00am | 12U/5S | KCSA 2014 BLACK vs CHICAGO UNITED 2014 LEGENDS | 32 | KCSA SOCCER FIELDS | |
| 3837* | Sat 10/4 12:30pm |
10U/5SE | CHICAGO UNITED 2016 FALCONS vs CFA - MIDWEST WINGS 2016/17 | 33 | ALTMAN PARK | 7v7 |
| 3994* | Sat 10/4 1:00pm | 9U/5S | CHICAGO UNITED 2017 STORM vs MT GREENWOOD KNIGHTS SC 2017 | 33 | CHIEF MIKE O'CONNELL PARK | |
| 4117 | Sat 10/4 2:00pm | 8U-7V7/5S | LEGACY 2018 vs CHICAGO UNITED 2018 WARRIORS | 26 | SPENCER SCHOOL CAMPUS | Field 11 - 7v7 |
| 3995 | Sun 10/5 1:00pm | 15U-FS/5S | CHICAGO UNITED 2011 EAGLES vs STORM SC 2011/12 | 33 | ALTMAN PARK | 11v11 |
| 4165 | Sun 10/5 3:00pm | 13U/5SE | CHICAGO UNITED 2013 TITANS vs CHICAGO EMPIRE FC SOUTH 13/14 BLUE | 33 | ALTMAN PARK | 11v11 |
| 86* | Fri 10/10 7:30pm* Submitted |
13U/5SE | KORA FC 2013 ELITE vs CHICAGO UNITED 2013 TITANS | 26 | CENTENNIAL PARK (ORLAND PARK) | Soccer 4 |
| 4401* | Sat 10/11 9:00am | 9U/5S | CHICAGO CITY 2017 SOUTH I vs CHICAGO UNITED 2017 STORM | 26 | EAGLE RIDGE II PARK | |
| 4511 | Sat 10/11 10:00am | 12U/5S | CHICAGO UNITED 2014 LEGENDS vs ORLAND PARK STING FC 2014 SELECT | 33 | ALTMAN PARK | 9v9 |
| 4543 | Sun 10/12 10:00am | 10U/5SE | RANGERS SOCCER ACADEMY 2016 vs CHICAGO UNITED 2016 FALCONS | 33 | ALTMAN PARK | |
| 2179* | Sun 10/12 12:00pm |
9U/5S | MWGFC 2017 ELITE vs CHICAGO UNITED 2017 STORM | 33 | KOSTNER PARK | |
| 4913 | Sun 10/12 1:15pm | 15U-FS/5S | WINDY CITY PRIDE 2011/12 vs CHICAGO UNITED 2011 EAGLES | 33 | HICKORY CREEK MIDDLE SCHOOL | |
| 3149* | Sun 10/12 2:00pm |
13U/5SE | MWGFC 2013 PREMIER vs CHICAGO UNITED 2013 TITANS | 33 | KOSTNER PARK | |
| 5139* | Sun 10/12 4:00pm | 8U-7V7/5S | EVERGREEN UNITED FC 2018/2019 vs CHICAGO UNITED 2018 WARRIORS | 17 | MACARTHUR PARK | |
| 5556 | Sat 10/18 11:30am | 10U/5SE | CHICAGO UNITED 2016 FALCONS vs ACADEMIA ATLAS FC 2016 BLACK | 33 | ALTMAN PARK | 7v7 |
| 5717 | Sat 10/18 1:00pm | 15U-FS/5S | LISLE FC 2011-2012 ASTON VILLA vs CHICAGO UNITED 2011 EAGLES | 18 | WOODGLEN PARK | 11v11 Field |
| 5852 | Sat 10/18 2:30pm | 8U-7V7/5S | CHICAGO UNITED 2018 WARRIORS vs LG CELTICS 2018/2019 BLACK | 33 | ALTMAN PARK | 7v7 |
| 5879 | Sun 10/19 3:00pm | 13U/5SE | CHICAGO UNITED 2013 TITANS vs WINDY CITY PRIDE 2013 | 33 | ALTMAN PARK | 11v11 |
| 6182 | Sat 10/25 9:00am | 12U/5S | UESC - VORTEX 14/15 BLUE vs CHICAGO UNITED 2014 LEGENDS | 33 | CACHEY PARK | |
| 6726* | Sat 10/25 10:00am |
8U-7V7/5S | CHICAGO UNITED 2018 WARRIORS vs EVERGREEN UNITED FC 2018/2019 | 33 | ALTMAN PARK | 7v7 |
| 6546 | Sat 10/25 1:00pm | 9U/5S | CHICAGO UNITED 2017 STORM vs TESC 2017 PREMIER GREEN | 33 | ALTMAN PARK | 7v7 |
| 6410 | Sun 10/26 12:00pm | 10U/5SE | CFA - MIDWEST WINGS 2016/17 vs CHICAGO UNITED 2016 FALCONS | 8 | BEECH PARK (INDIANA) | |
| 6878 | Sun 10/26 4:00pm | 15U-FS/5S | MIDWEST ELITE SC 2011 vs CHICAGO UNITED 2011 EAGLES | 17 | HARVERSTER PARK |