| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 3222 | Sun 9/28 2:00pm | 14U/3CITY | CHICAGO KICS 2012 PRE-ACADEMY (CITY) vs NW 2012B PREMIER I | 25 | ST. IGNATIUS HS | |
| 5448* | Sun 9/28 4:00pm |
11U/5CITY | IPROSKILLS 2015 BLUE vs CHICAGO KICS 2015 RED (CITY) | 16 | LERNER PARK | |
| 3999* | Sat 10/4 9:00am |
10U/5CITY1 | CHICAGO KICS 2016 BLUE (CITY) vs OPRF ALLIANCE 2016 | 25 | DUNBAR GRASS | 7 v 7 |
| 3656 | Sat 10/4 9:15am | 14U/5E1 | CHICAGO CITY 2012 LOOP I vs CHICAGO KICS 2012 WHITE (CITY) | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | 11v11 |
| 1657 | Sat 10/4 10:00am | 9U/5CITY | CHICAGO KICS 2017 WHITE (CITY) vs CHICAGO KNIGHTS 2017/2018 | 25 | DUNBAR GRASS | 7 v 7 |
| 2967* | Sat 10/4 10:15am |
9U/4S | UESC - VORTEX 2017/2018 vs CHICAGO KICS 2017 BLUE (SOUTH) | 33 | CACHEY PARK | |
| 3804 | Sat 10/4 11:00am | 12U/3CITY | IPROSKILLS 2014 SELECT ACADEMY vs CHICAGO KICS 2014 PRE-ACADEMY (CITY) | 16 | LERNER PARK | |
| 3787* | Sat 10/4 11:00am | 15U-FS/5NE | RUSH NORTH SHORE 2011 PREMIER vs CHICAGO KICS 2011 PRE-ACADEMY I (CITY) | 16 | WILLOW HILL PARK | Field #3 |
| 4390* | Sat 10/4 12:00pm |
8U-5V5/5S1 | CHICAGO KICS 2018 BLUE (CITY) vs WEST LAWN SOCCER CLUB 2018/19 | 25 | DUNBAR GRASS | 5 v 5 |
| 1783* | Sat 10/4 1:00pm |
8U-5V5/4S | CHICAGO KICS 2018 BLACK (CITY) vs ORLAND PARK STING FC 2018 PREMIER | 25 | DUNBAR GRASS | 5 v 5 |
| 3673* | Sat 10/4 1:30pm |
12U/5CITY | BERBER CITY FC 2014 vs CHICAGO KICS 2014 RED (CITY) | 32 | DUNBAR SOCCER COMPLEX | |
| 4101 | Sat 10/4 2:00pm | 9U/5CITY | CHICAGO KICS 2017 BLUE (CITY) vs CFYSC 2017B SELECT WHITE | 25 | DUNBAR GRASS | 7 v 7 |
| 4245 | Sat 10/4 3:30pm | 12U/3CITY | CFYSC 2014B SELECT WHITE vs CHICAGO KICS 2014 BLUE (CITY) | 17 | FIRE PITCH | 9v9 Pitch 1-B |
| 4318 | Sat 10/4 4:30pm | 11U/5CITY | NW 2015B PREMIER III vs CHICAGO KICS 2015 RED (CITY) | 17 | UIC TURF FIELD EAST | |
| 4336* | Sat 10/4 4:30pm | 12U/4S | PSG ACADEMY LEMONT 2014 vs CHICAGO KICS 2014 BLACK (SOUTH) | 17 | CENTENNIAL PARK (LEMONT) | |
| 5479* | Sat 10/4 4:30pm |
8U-5V5/5S2 | CHICAGO KICS 2018 WHITE (CITY) vs RANGERS SOCCER ACADEMY 2018 | 25 | DUNBAR GRASS | 5 v 5 |
| 4175* | Sat 10/4 5:30pm |
13U/4CITY | CHICAGO KICS 2013 WHITE (CITY) vs ACADEMIA ATLAS 2013 BLACK | 25 | ST. IGNATIUS HS |