| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 1236* | Tue 5/26 6:00pm |
11U/1N | CFYSC 2015B PREMIER RED vs CFYSC 2015B PREMIER | 17 | FIRE PITCH | |
| 6621* | Sat 5/30 8:30am |
12U/3E | OLYMPIACOS 2014 ELITE vs CFYSC 2014B SELECT WHITE | 4 | MAIN EAST HIGH SCHOOL | 9v9 |
| 6290* | Sat 5/30 10:00am |
9U/3E | CHICAGO CELTIC SC 2017 GREEN vs CFYSC 2017B SELECT | 4 | HITCH ELEMENTARY SCHOOL | |
| 228* | Sat 5/30 10:15am |
8U-5V5/4N | CFYSC 2019B SELECT vs EGSC 2018 ELITE | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 377* | Sat 5/30 10:15am |
11U/1N | CFYSC 2015B PREMIER RED vs CHICAGO FC UNITED 2015 ACADEMY TEAM I | 17 | FIRE PITCH | 9v9 Pitch 1-A |
| 6170 | Sat 5/30 10:15am | 11U/4E2 | CFYSC 2016B PREMIER RED vs OLYMPIACOS 2015 PREMIER | 17 | FIRE PITCH | 9v9 Pitch 1-A |
| 6214 | Sat 5/30 10:30am | 8U-5V5/5E | SCOTTISH SOCCER ACADEMY 2018 vs CFYSC 2018B SELECT NAVY | 16 | SKOKIE WASHBURNE | |
| 6180 | Sat 5/30 10:30am | 12U/4CITY2 | CHICAGO CELTIC SC 2014 WHITE vs CFYSC 2014B SELECT RED | 4 | EDISON PARK ELEMENTARY | |
| 3216* | Sat 5/30 11:30am |
8U-7V7/5E1 | CFYSC 2018B SELECT WHITE vs CHICAGO CITY 2018 II | 17 | FIRE PITCH | PITCH 2V |
| 6289 | Sat 5/30 11:30am | 9U/4CITY | CFYSC 2018B SELECT RED vs CHICAGO KICS 2017 BLACK (CITY) | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 6470* | Sat 5/30 12:00pm |
13U/2E | PSG ACADEMY CHICAGO 2013 PRE-ACADEMY vs CFYSC 2014B PREMIER | 16 | WHITNEY YOUNG HS TURF | 1 |
| 6400 | Sat 5/30 12:30pm | 9U/4CITY | CHICAGO CITY 2017 ACADEMY II vs CFYSC 2017B SELECT WHITE | 16 | BRITISH SCHOOL TURF | |
| 1368* | Sat 5/30 12:45pm |
9U/1 | CFYSC 2017B PREMIER RED vs CSA 2017 B BLUE | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 6477* | Sat 5/30 1:30pm |
9U/5CITY | PSG ACADEMY CHICAGO 2017 BLUE II vs CFYSC 2017B SELECT RED | 16 | JAMES OTIS SCHOOL FIELD - ONLY 7V7 GAMES | |
| 645* | Sat 5/30 2:00pm |
10U/3CITY | CFYSC 2016B SELECT vs CHICAGO CITY 2016 ACADEMY II | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 6662* | Sat 5/30 3:00pm | 11U/3E | RUSH - WILMETTE WINGS 2015 BLUE vs CFYSC 2015B SELECT | 16 | WILMETTE COMMUNITY PLAYFIELD | 3 |
| 6745 | Sat 5/30 3:15pm | 10U/4CITY | CFYSC 2016B SELECT RED vs IPROSKILLS 2016 BLUE | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 6750* | Sat 5/30 3:30pm | 11U/1N | AAC EAGLES CHICAGO 2015 WHITE vs CFYSC 2015B PREMIER | 7 | HANSON FIELD | |
| 6790* | Sat 5/30 4:00pm | 15U-SPRING/3N | PEGASUS FC/1974 2011 BLACK vs CFYSC 2011B PREMIER WHITE | 16 | TRINITY UNIVERSITY | 11v11 |
| 6894* | Sat 5/30 4:30pm |
16U/3CITY | CHICAGO KICS 2010 PA II (CITY) vs CFYSC 2010B PREMIER WHITE | 25 | ST IGNATIUS HS | |
| 6818* | Sat 5/30 5:00pm |
13U/3E | CFYSC 2013B SELECT vs CHICAGO KICS 2013 PRE-ACADEMY (CITY) | 17 | MONTROSE FIELD | |
| 2976* | Sat 5/30 6:45pm |
17U/3CITY | CFYSC 2009B PREMIER WHITE vs FC STARS POWERSTRIKERS 2009 RED | 17 | MONTROSE FIELD | |
| 6089* | Sat 5/30 7:00pm |
14U/4CITY | CFYSC 2012B SELECT vs CHICAGO CITY 2012 LOOP I | 17 | CLARK PARK | |
| 4481* | Sun 5/31 7:30am |
9U/4CITY | CFYSC 2017B SELECT WHITE vs PSG ACADEMY CHICAGO 2017 RED | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 7278* | Sun 5/31 7:30am |
9U/4CITY | CFYSC 2018B SELECT RED vs YSI FC 2017 | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 7598* | Sun 5/31 8:00am |
9U/1 | LASC 2017 PREMIER vs CFYSC 2017B PREMIER RED | 16 | LAKE VILLA TOWNSHIP SOCCER COMPLEX | Field A - 7v7 |
| 4471* | Sun 5/31 9:00am |
11U/1N | PEGASUS FC/1974 2015 RED vs CFYSC 2015B PREMIER | 16 | WILLOW HILL PARK | 2B |
| 1574* | Sun 5/31 10:00am |
8U-5V5/4N | WCOB FC 2018 SELECT vs CFYSC 2019B SELECT | 17 | CENTRAL PARK FIELDS - FOREST GATE RD. ENTRANCE | Field 9 |
| 6133* | Sun 5/31 10:00am |
10U/3CITY | IPROSKILLS 2016 BLACK vs CFYSC 2016B SELECT | 16 | ROGERS PARK | #2 |
| 6227 | Sun 5/31 10:50am | 16U/3CITY | OPRF ALLIANCE 2010/11 vs CFYSC 2010B PREMIER WHITE | 12 | TRITON COLLEGE | |
| 6816* | Sun 5/31 12:00pm |
10U/4CITY | CHICAGO CITY 2016 II vs CFYSC 2016B SELECT WHITE | 16 | BERNARD ZELL ANSHE EMET DAY SCHOOL | |
| 7281* | Sun 5/31 12:30pm | 15U-SPRING/3N | CHICAGO MAGIC 2011 ELITE vs CFYSC 2011B PREMIER WHITE | 16 | DANNY CUNNIFF | North Large |
| 6505* | Sun 5/31 1:00pm | 17U/3CITY | FC STARS 2009 PREMIER vs CFYSC 2009B PREMIER WHITE | 16 | NILES WEST HIGH SCHOOL | 2 |
| 6452 | Sun 5/31 1:00pm | 8U-7V7/5E1 | FC-1 ACADEMY 2019 ELITE vs CFYSC 2018B SELECT WHITE | 16 | COMMUNITY PARK WEST (GLENVIEW) | 7 - (7v7) |
| 7355* | Sun 5/31 1:00pm |
11U/3E | PRSC 2015 ORANGE II vs CFYSC 2015B SELECT RED | 4 | WOODLAND PARK | SE |
| 3618* | Sun 5/31 1:30pm |
12U/4CITY2 | NW 2014B PREMIER II vs CFYSC 2014B SELECT RED | 17 | UIC TURF FIELD EAST | |
| 6603* | Sun 5/31 2:00pm |
11U/2CITY | PSG ACADEMY CHICAGO 2015 PRE-ACADEMY vs CFYSC 2015B PREMIER WHITE | 16 | LIVINGSTON FIELD - USE FOR 9V9 GAMES ONLY - FALL 2025 | 1 |
| 2971* | Sun 5/31 2:30pm |
14U/4CITY | CFYSC 2012B SELECT vs NW 2012B PREMIER II | 17 | MONTROSE FIELD | |
| 5119* | Sun 5/31 3:00pm |
10U/2E | CHICAGO CITY 2016 ACADEMY I vs CFYSC 2017B PREMIER | 16 | BERNARD ZELL ANSHE EMET DAY SCHOOL | |
| 551* | Sun 5/31 3:30pm |
12U/4CITY1 | PSG ACADEMY CHICAGO 2014 RED vs CFYSC 2014B SELECT | 16 | LIVINGSTON FIELD - USE FOR 9V9 GAMES ONLY - FALL 2025 | |
| 7700* | Sun 5/31 5:00pm |
13U/2E | IP-SKOMOR 2013 PREMIER vs CFYSC 2014B PREMIER | 16 | GOLF MIDDLE SCHOOL |