| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 472* | Sat 9/6 11:20am |
9U/4CITY | YSI FC 2017 vs CFYSC 2017B SELECT | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 307* | Sat 9/6 12:00pm |
7U-4V4/N | PSG ACADEMY CHICAGO 2019 WHITE vs YSI FC 2019 | 66 | SKINNER PARK - DO NOT USE | |
| 659* | Sun 9/7 10:00am |
8U-7V7/4E | YSI FC 2018 vs 60 UNITED - VHSC 2018 BLUE | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 473* | Sun 9/7 11:10am |
10U/3E | YSI FC 2016 vs CFYSC 2016B SELECT | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 416 | Sun 9/7 12:00pm | 11U/4CITY | NW 2015B PREMIER II vs YSI FC 2015 | 17 | UIC TURF FIELD EAST | |
| 844* | Sun 9/7 5:00pm | 12U/2E | PSG ACADEMY CHICAGO 2014 PRE-ACADEMY vs YSI FC 2014 | 16 | CRANE HIGH SCHOOL - USE FOR 9V9 GAMES ONLY | |
| 1502 | Sat 9/13 2:00pm | 12U/2E | PRSC 2014 ORANGE vs YSI FC 2014 | 4 | WOODLAND PARK | NE |
| 3980* | Sat 9/13 2:50pm |
9U/4CITY | YSI FC 2017 vs IPROSKILLS 2017 | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 1140* | Sat 9/13 3:00pm |
8U-7V7/4E | PRSC 2018 ORANGE vs YSI FC 2018 | 4 | EMERSON MIDDLE SCHOOL | NE |
| 3981* | Sun 9/14 9:00am |
10U/3E | YSI FC 2016 vs FCS TEAM EVANSTON 2016 BOYS ORANGE II | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 1408* | Sun 9/14 12:30pm |
9U/4CITY | PSG ACADEMY CHICAGO 2017 RED vs YSI FC 2017 | 16 | JAMES OTIS SCHOOL FIELD - ONLY 7V7 GAMES | |
| 1049 | Sun 9/14 1:30pm | 11U/4CITY | CHICAGO KICS 2015 BLUE (CITY) vs YSI FC 2015 | 25 | DUNBAR GRASS | 9 v 9 |
| 2075 | Sat 9/20 11:20am | 7U-4V4/N | YSI FC 2019 vs PSG ACADEMY CHICAGO 2019 CITY NORTH | 66 | ALCOTT ELEMENTARY SCHOOL | |
| 2228 | Sat 9/20 12:40pm | 12U/2E | YSI FC 2014 vs CHICAGO CITY 2014 ACADEMY II | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 2226* | Sat 9/20 1:40pm |
10U/3E | YSI FC 2016 vs NW 2016B PREMIER I | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 2413 | Sat 9/20 2:50pm | 8U-7V7/4E | YSI FC 2018 vs PRSC 2018 ORANGE | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 2225* | Sun 9/21 11:00am |
9U/4CITY | YSI FC 2017 vs NW 2017B PREMIER I | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 2076* | Sun 9/21 11:40am |
11U/4CITY | YSI FC 2015 vs CHICAGO CITY 2015 LOOP I | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 5639* | Sun 9/21 4:30pm |
10U/3E | PRSC 2016 ORANGE vs YSI FC 2016 | 4 | EMERSON MIDDLE SCHOOL | NC |
| 3089 | Sat 9/27 12:30pm | 9U/4CITY | CHICAGO CITY 2017 ACADEMY II vs YSI FC 2017 | 16 | BRITISH SCHOOL TURF | |
| 3389 | Sat 9/27 3:15pm | 10U/3E | CFYSC 2017B PREMIER vs YSI FC 2016 | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 3436 | Sat 9/27 4:00pm | 7U-4V4/N | NSFC 2019/2020 vs YSI FC 2019 | 66 | LAKE FOREST HIGH SCHOOL WEST CAMPUS | Field 6 (4v4) |
| 2663* | Sat 9/27 4:45pm |
8U-7V7/4E | CHICAGO CITY 2018 I vs YSI FC 2018 | 16 | LA SALLE LANGUAGE ACADEMY | |
| 3456* | Sat 9/27 5:00pm |
11U/4CITY | CHICAGO CITY 2015 II vs YSI FC 2015 | 16 | BRITISH SCHOOL TURF | |
| 3835 | Sat 10/4 11:20am | 11U/4CITY | YSI FC 2015 vs CFYSC 2015B SELECT RED | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 3983 | Sat 10/4 12:40pm | 12U/2E | YSI FC 2014 vs CFA- JAHBAT FC B2014 GREEN | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 5687* | Sun 10/5 11:40am |
12U/2E | YSI FC 2014 vs IPROSKILLS 2014 NEON | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 4690 | Sat 10/11 11:20am | 11U/4CITY | YSI FC 2015 vs CHICAGO CITY 2015 I | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 4835 | Sat 10/11 12:30pm | 9U/4CITY | YSI FC 2017 vs CHICAGO KICS 2017 BLACK (CITY) | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 5019 | Sat 10/11 2:50pm | 8U-7V7/4E | YSI FC 2018 vs RUSH - WILMETTE WINGS 2018 PREMIER | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 6346* | Sat 10/11 3:30pm |
10U/3E | FC STARS 2016B BLACK vs YSI FC 2016 | 16 | NILES WEST HIGH SCHOOL | Grass Fields 2 |
| 4838* | Sun 10/12 9:00am |
12U/2E | YSI FC 2014 vs CHICAGO EDGE B2014 PRE-PREMIER XI | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 4157* | Sun 10/12 9:00am |
8U-7V7/4E | YSI FC 2018 vs ELA ELITE 2018 | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 5554 | Sat 10/18 11:20am | 7U-4V4/N | YSI FC 2019 vs CFYSC 2019B SELECT | 66 | ALCOTT ELEMENTARY SCHOOL | |
| 5736 | Sat 10/18 1:00pm | 8U-7V7/4E | 60 UNITED - VHSC 2018 BLUE vs YSI FC 2018 | 1 | VERNON HILLS ATHLETIC COMPLEX | Field 12 North Turf |
| 4693* | Sun 10/19 7:30am |
9U/4CITY | CFYSC 2017B SELECT vs YSI FC 2017 | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 5555* | Sun 10/19 11:40am |
11U/4CITY | YSI FC 2015 vs CFYSC 2015B SELECT | 17 | HAWTHORNE SCHOLASTIC ACADEMY | |
| 4836* | Sun 10/19 12:00pm |
10U/3E | YSI FC 2016 vs PSG ACADEMY CHICAGO 2016 RED | 17 | ALCOTT ELEMENTARY SCHOOL | |
| 6418* | Sat 10/25 12:45pm |
9U/4CITY | CHICAGO KICS 2017 BLACK (CITY) vs YSI FC 2017 | 25 | DUNBAR GRASS | 7 v 7 |
| 6069* | Sat 10/25 3:00pm | 8U-7V7/4E | RUSH - WILMETTE WINGS 2018 PREMIER vs YSI FC 2018 | 16 | HOWARD PARK | |
| 6798 | Sat 10/25 3:00pm | 7U-4V4/N | PSG ACADEMY CHICAGO 2019 CITY NORTH vs YSI FC 2019 | 66 | SKYLINE PITCH - ONLY 5V5 GAMES | |
| 6934 | Sat 10/25 5:00pm | 12U/2E | CHICAGO CITY 2014 ACADEMY II vs YSI FC 2014 | 16 | BRITISH SCHOOL TURF | |
| 6427* | Sun 10/26 10:30am |
10U/3E | CHICAGO CITY 2016 ACADEMY II vs YSI FC 2016 | 16 | BERNARD ZELL ANSHE EMET DAY SCHOOL | |
| 6884* | Sun 10/26 3:30pm |
11U/4CITY | PSG ACADEMY CHICAGO 2015 BLUE vs YSI FC 2015 | 16 | CRANE HIGH SCHOOL - USE FOR 9V9 GAMES ONLY | |
| 3834* | Sat 11/1 9:00am |
7U-4V4/N | YSI FC 2019 vs NORRIDGE UNITED 2019 PREMIER | 66 | ALCOTT ELEMENTARY SCHOOL | |
| 4689* | Sat 11/1 10:10am |
7U-4V4/N | YSI FC 2019 vs NORRIDGE UNITED 2019 SELECT | 66 | ALCOTT ELEMENTARY SCHOOL | |
| 3263* | Sat 11/1 12:00pm |
12U/2E | CFYSC 2014B PREMIER RED vs YSI FC 2014 | 17 | FIRE PITCH | 9v9 Pitch 1-B |
| 1214* | Sun 11/2 11:00pm | 7U-4V4/N | PSG ACADEMY CHICAGO 2019 GREEN vs YSI FC 2019 | 66 | CHICAGO HOPE ACADEMY TRACK & FIELD - USE FOR 5V5 & 7V7 GAMES |