| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 10* | Sat 9/12 2:00pm |
U08-5V5/5NW1 | SAA UNITED SC 2018/19 vs VCF ACADEMY CHICAGO 18/19 PETITES | 7 | OLYMPIC PARK FIELD | 8a (one half of fiel |
| 701* | Sat 9/12 6:00pm | U11/5N2 | VCF ACADEMY CHICAGO 15/16 SENYERA vs WINDY CITY FC 15/16 | 7 | HUNTINGTON CHASE | |
| 1* | Sun 9/13 1:00pm | U13/5NW1 | VCF ACADEMY CHICAGO 13/14 AMUNT vs WINDY CITY FC 13/14 | 7 | WINDEMERE PARK | |
| 3262* | Sun 9/13 4:00pm |
U10/5NW2 | ELA ELITE 16/17 COMPETITIVE vs VCF ACADEMY CHICAGO 16/17 TARONJA | 7 | DEER PARK TOWN CENTER | 7v7 |
| 5187* | Sat 9/19 2:00pm rainout |
U13/5NW1 | VCF ACADEMY CHICAGO 13/14 AMUNT vs ESCO F.C. 2013/14 BLACK | 7 | WINDEMERE PARK | |
| 1136* | Sun 9/20 4:00pm | U11/5N2 | IP-ARLINGTON ACES 15/16 GREEN 2 vs VCF ACADEMY CHICAGO 15/16 SENYERA | 7 | PRAIRIE PK | |
| 2084 | Sat 9/26 3:00pm | U08-5V5/5NW1 | FC LAKE COUNTY 18/19 GREEN vs VCF ACADEMY CHICAGO 18/19 PETITES | 16 | ALLEGHANY PARK | AH 13 |
| 2143* | Sat 9/26 6:00pm |
U09/5NW3 | VCF ACADEMY CHICAGO 17/18 BLANC vs PALATINE CELTIC 17/18 GREEN | 7 | DIVINE SAVIOR CHURCH | |
| 2023* | Sun 9/27 1:00pm | U10/5NW2 | AAC EAGLES CHICAGO 16/17 SILVER vs VCF ACADEMY CHICAGO 16/17 TARONJA | 7 | ADOLPH LINK FIELDS | North |
| 2783 | Sat 10/3 2:00pm | U08-5V5/5NW1 | VCF ACADEMY CHICAGO 18/19 PETITES vs FC LAKE COUNTY 18/19 BLUE | 7 | DIVINE SAVIOR CHURCH | |
| 3004* | Sat 10/3 4:00pm |
U10/5NW2 | VCF ACADEMY CHICAGO 16/17 TARONJA vs PALATINE CELTIC 16/17 GREEN | 7 | DIVINE SAVIOR CHURCH | |
| 1371* | Sun 10/4 1:00pm |
U10/5NW2 | FORCE 16/17B PREMIER vs VCF ACADEMY CHICAGO 16/17 TARONJA | 14 | LIPPOLD PARK SOCCER COMPLEX | FIELD 6 |
| 2882 | Sun 10/4 3:00pm | U09/5NW3 | ELITE S.C. 2017/18 RED vs VCF ACADEMY CHICAGO 17/18 BLANC | 7 | HERITAGE PARK (WHEELING) | #12 7v7 |
| 2229* | Sun 10/4 5:00pm | U13/5NW1 | VCF ACADEMY CHICAGO 13/14 AMUNT vs PRSC 13/14 SILVER 2 | 7 | WINDEMERE PARK | |
| 3395* | Sat 10/10 3:00pm |
U09/5NW3 | ELA ELITE 17/18 COMPETITIVE vs VCF ACADEMY CHICAGO 17/18 BLANC | 7 | DEER PARK TOWN CENTER | 7v7 |
| 3341* | Sat 10/10 5:00pm |
U08-5V5/5NW1 | CARY DEFENDERS 18/19 vs VCF ACADEMY CHICAGO 18/19 PETITES | 14 | CARY GROVE PARK | SOUTH |
| 3335* | Sun 10/11 1:00pm |
U11/5N2 | FC LAKE COUNTY 15/16 SELECT 2 vs VCF ACADEMY CHICAGO 15/16 SENYERA | 16 | ALLEGHANY PARK | AH 4 |
| 3454* | Sun 10/11 4:00pm |
U13/5NW1 | IP- ARLINGTON ACES 13/14 GREEN vs VCF ACADEMY CHICAGO 13/14 AMUNT | 7 | SUNSET MEADOWS | |
| 5756* | Sun 10/11 6:00pm | U08-5V5/5NW1 | VCF ACADEMY CHICAGO 18/19 PETITES vs FC LAKE COUNTY 18/19 GREEN | 7 | PRAIRIE LAKES PK FLDS | 5v5 |
| 4253 | Sat 10/17 2:00pm | U08-5V5/5NW1 | VCF ACADEMY CHICAGO 18/19 PETITES vs SAA UNITED SC 2018/19 | 7 | DIVINE SAVIOR CHURCH | |
| 4409 | Sat 10/17 4:00pm | U09/5NW3 | BARCA ACADEMY CHICAGO 17/18 GRANA vs VCF ACADEMY CHICAGO 17/18 BLANC | 7 | OLYMPIC PARK FIELD | Field 5 |
| 4470* | Sat 10/17 7:00pm |
U10/5NW2 | VCF ACADEMY CHICAGO 16/17 TARONJA vs SAA UNITED SC 16/17 GOLD | 7 | DIVINE SAVIOR CHURCH | |
| 3724* | Sun 10/18 1:00pm | U13/5NW1 | VCF ACADEMY CHICAGO 13/14 AMUNT vs SAA UNITED SC 13/14 GOLD | 7 | WINDEMERE PARK | |
| 3978* | Sun 10/18 4:00pm |
U11/5N2 | ELA ELITE 15/16 COMPETITIVE vs VCF ACADEMY CHICAGO 15/16 SENYERA | 7 | VEHE PK | |
| 957* | Sun 10/18 7:00pm | U09/5NW3 | HAWTHORN WOODS ELITE 17/18 GREEN vs VCF ACADEMY CHICAGO 17/18 BLANC | 7 | HERITAGE OAKS | |
| 5166* | Sat 10/24 1:00pm | U11/5N2 | VCF ACADEMY CHICAGO 15/16 SENYERA vs PEGASUS FC 15/16 WHITE | 7 | HUNTINGTON CHASE | |
| 1319* | Sat 10/24 4:00pm |
U13/5NW1 | PEGASUS FC 13/14 WHITE vs VCF ACADEMY CHICAGO 13/14 AMUNT | 16 | CLAVEY PARK | Large |
| 5174* | Sat 10/24 6:30pm |
U10/5NW2 | BARCA ACADEMY CHICAGO 16/17 GRANA vs VCF ACADEMY CHICAGO 16/17 TARONJA | 7 | OLYMPIC PARK FIELD | Field 7 |
| 4524* | Sun 10/25 2:00pm |
U08-5V5/5NW1 | PEGASUS FC 19/20 RED vs VCF ACADEMY CHICAGO 18/19 PETITES | 16 | TRINITY UNIVERSITY | 5v5 |
| 5128* | Sun 10/25 4:30pm |
U09/5NW3 | VCF ACADEMY CHICAGO 17/18 BLANC vs RUSH NORTH 17/18 BLUE | 7 | DIVINE SAVIOR CHURCH | |
| 2192* | Sun 10/25 6:30pm | U11/5N2 | VCF ACADEMY CHICAGO 15/16 SENYERA vs PALATINE CELTIC 15/16 WHITE | 7 | METRO MAJEWSKI PARK | Field 5 |
| 2161* | Fri 10/30 7:30pm |
U13/5NW1 | PEGASUS FC 13/14 WHITE vs VCF ACADEMY CHICAGO 13/14 AMUNT | 16 | BRICKYARD | |
| 5904* | Sat 10/31 2:00pm |
U09/5NW3 | VCF ACADEMY CHICAGO 17/18 BLANC vs SAA UNITED SC 17/18 GOLD | 7 | DIVINE SAVIOR CHURCH | |
| 5959* | Sat 10/31 4:00pm |
U10/5NW2 | VCF ACADEMY CHICAGO 16/17 TARONJA vs BARCA ACADEMY CHICAGO 16/17 GRANA | 7 | DIVINE SAVIOR CHURCH | |
| 1276* | Sat 10/31 5:30pm |
U08-5V5/5NW1 | VCF ACADEMY CHICAGO 18/19 PETITES vs PEGASUS FC 19/20 RED | 7 | DIVINE SAVIOR CHURCH | |
| 5944* | Sun 11/1 1:00pm | U11/5N2 | VCF ACADEMY CHICAGO 15/16 SENYERA vs RUSH NORTH 15/16 BLUE | 7 | HUNTINGTON CHASE | |
| 654* | Sun 11/1 3:30pm |
U09/5NW3 | VCF ACADEMY CHICAGO 17/18 BLANC vs JOM SC 17/18 WHITE | 7 | DIVINE SAVIOR CHURCH | |
| 4697* | Sat 11/7 1:30pm | U13/5NW1 | ESCO F.C. 2013/14 BLACK vs VCF ACADEMY CHICAGO 13/14 AMUNT | 7 | PRAIRIE LAKES PK FLDS | Field #1 - 11v11 |
| 724* | Sat 11/7 4:00pm | U10/5NW2 | VCF ACADEMY CHICAGO 16/17 TARONJA vs ELITE S.C. 2016/17 RED | 7 | PRAIRIE LAKES PK FLDS | |
| 2625* | Sun 11/8 1:30pm |
U11/5N2 | ELITE S.C. 2015/16 WHITE vs VCF ACADEMY CHICAGO 15/16 SENYERA | 7 | HERITAGE PARK (WHEELING) | #8 9v9 |