| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 5354* | Fri 10/10 7:30pm |
13U/4CITY | CHICAGO CITY 2013 LOOP I vs IPROSKILLS 2013 BLACK | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | |
| 4435 | Sat 10/11 9:00am | 12U/4E | IPROSKILLS 2014 BLACK vs IP-SKOMOR 2014 PREMIER II | 16 | ROGERS PARK | #3 |
| 4565 | Sat 10/11 10:15am | 11U/3CITY | CFYSC 2016B PREMIER vs IPROSKILLS 2015 BLACK | 17 | FIRE PITCH | 9v9 Pitch 1-B |
| 967* | Sat 10/11 11:00am |
13U/4CITY | IPROSKILLS 2013 BLACK vs NW 2013B PREMIER II | 16 | ROGERS PARK | |
| 4618* | Sat 10/11 11:00am |
10U/4CITY | CHICAGO KICS 2016 BLACK (CITY) vs IPROSKILLS 2016 BLACK | 25 | DUNBAR GRASS | 7 v 7 |
| 4742 | Sat 10/11 12:00pm | 8U-7V7/5E2 | CHICAGO CITY 2018 III vs IPROSKILLS 2018 | 16 | LA SALLE LANGUAGE ACADEMY | 7v7 |
| 1844* | Sat 10/11 2:00pm | 11U/1N | PEGASUS FC/1974 (2015) RED vs IPROSKILLS 2015 NEON | 16 | CLAVEY PARK | Med |
| 4663* | Sat 10/11 4:00pm | 12U/3CITY | IPROSKILLS 2014 SELECT ACADEMY vs CHICAGO CITY 2014 I | 16 | LERNER PARK | |
| 6451* | Sat 10/11 4:30pm |
10U/4CITY | IPROSKILLS 2016 BLUE vs CHICAGO CITY 2016 I | 16 | ROGERS PARK | #2 |
| 5308* | Sun 10/12 9:00am |
14U/4E | IPROSKILLS 2012 BLACK vs FC MIRAGE 2012 | 16 | ROGERS PARK | |
| 4354* | Sun 10/12 10:30am | 13U/1 | IPROSKILLS 2013 NEON vs SAA UNITED SC 2013 BLACK | 16 | ROGERS PARK | |
| 4626 | Sun 10/12 11:00am | 11U/5CITY | BERBER CITY FC 2015 vs IPROSKILLS 2015 BLUE | 32 | DUNBAR SOCCER COMPLEX | |
| 4912 | Sun 10/12 1:15pm | 10U/4CITY | NW 2016B PREMIER II vs IPROSKILLS 2016 BLUE | 17 | FOSTER AVENUE FIELDS | II |
| 5098* | Sun 10/12 3:00pm | 14U/1 | SPIDERS FC 2012 vs IPROSKILLS 2012 NEON | 6 | PRAIRIE FEST PARK | FIELD # 9 |
| 503* | Sun 10/12 4:00pm |
10U/4CITY | FC STARS POWERSTRIKERS 2016B vs IPROSKILLS 2016 BLACK | 16 | NORTHEASTERN IL UNIVERSITY | |
| 5176* | Sun 10/12 4:30pm | 15U-FS/4E | NW 2011B PREMIER FS vs IPROSKILLS 2011 BLACK | 17 | FOSTER AVENUE FIELDS | 1 |