| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 1081* | Sat 9/13 1:30pm |
14U/5SW | ORLAND PARK STING FC 2012 ELITE 2 vs CRESTWOOD SC 2012 | 26 | SCHUSSLER PARK | Blue Turf #1 |
| 1801* | Sun 9/14 1:30pm |
14U/5SW | CRESTWOOD SC 2012 vs ORLAND PARK STING FC 2012 ELITE 2 | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 2973* | Sun 9/14 4:15pm |
13U/5SE | WINDY CITY PRIDE 2013 vs CRESTWOOD SC 2013/14 | 33 | HICKORY CREEK MIDDLE SCHOOL | |
| 50* | Sun 9/21 1:30pm |
14U/5SW | CRESTWOOD SC 2012 vs CHICAGO BLAST 2012 GOLD | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 2866* | Sun 9/28 3:00pm |
14U/5SW | GALAXY 2012 SELECT BLUE vs CRESTWOOD SC 2012 | 6 | FRONTIER PARK (NAPERVILLE) | Field E - Large |
| 6753* | Sun 9/28 5:00pm | 13U/5SE | CHICAGO UNITED 2013 TITANS vs CRESTWOOD SC 2013/14 | 33 | FREEDOM FIELD (TINLEY PARK) | |
| 3570* | Sat 10/4 1:00pm | 14U/5SW | CRESTWOOD SC 2012 vs UESC- CHICAGOLAND 2012 PREM FF | 33 | SHEPARD HIGH SCHOOL TURF | |
| 3895* | Sat 10/4 3:00pm |
13U/5SE | CRESTWOOD SC 2013/14 vs KORA FC 2013 ELITE | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 4403* | Sun 10/5 1:00pm | 14U/5SW | CRESTWOOD SC 2012 vs NAPERVILLE EAGLES 2012 FURY | 33 | SHEPARD HIGH SCHOOL TURF | |
| 5623* | Sat 10/18 12:00pm | 13U/5SE | MUSTANGS UNITED FC 2013 vs CRESTWOOD SC 2013/14 | 17 | FITZGERALD PARK | |
| 6024 | Sat 10/18 5:00pm | 14U/5SW | CHICAGO BLAST 2012 GOLD vs CRESTWOOD SC 2012 | 17 | OAK BROOK PARK DISTRICT | |
| 6547 | Sat 10/25 1:00pm | 13U/5SE | CHICAGO EMPIRE FC SOUTH 13/14 BLUE vs CRESTWOOD SC 2013/14 | 33 | CAESAR PARK | 11v11 |
| 6911 | Sat 10/25 4:30pm | 14U/5SW | NAPERVILLE EAGLES 2012 FURY vs CRESTWOOD SC 2012 | 6 | FRONTIER PARK (NAPERVILLE) | |
| 377* | Sun 10/26 4:00pm |
13U/5SE | CRESTWOOD SC 2013/14 vs ACADEMIA ATLAS 2013/14 RED | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 2145* | Sat 11/1 1:00pm |
13U/5SE | CRESTWOOD SC 2013/14 vs MWGFC 2013 PREMIER | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 4750* | Sun 11/2 11:00am |
13U/5SE | CRESTWOOD SC 2013/14 vs ORLAND PARK STING FC 2013 SELECT 2 | 33 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |