| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 390 | Sat 4/11 12:00pm | 14U/5S | CHICAGO EMPIRE FC 2012 BLUE vs CRESTWOOD SC 2012 | 17 | OAK BROOK POLO FIELDS | C 11v11 |
| 173* | Sat 4/11 1:00pm | 13U/5S | CRESTWOOD SC 2013/14 vs ORLAND PARK STING FC 2013 SELECT 2 | 26 | SHEPARD HIGH SCHOOL TURF | Shepard |
| 5514* | Sun 4/12 1:00pm |
14U/5S | LG CELTICS 2012 GREEN vs CRESTWOOD SC 2012 | 17 | LYONS TOWNSHIP HS NORTH CAMPUS | Gilbert and Cossitt |
| 1231* | Sat 4/18 12:30pm |
10U/5S2 | CRESTWOOD SC 2016 vs UESC - VORTEX 2016 | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 2311 | Sat 4/25 11:00am | 10U/5S2 | UESC - HF VIKINGS 2016 RED vs CRESTWOOD SC 2016 | 35 | BICENTENNIAL PARK | |
| 2055* | Sat 4/25 3:00pm |
14U/5S | CSA 2012 B WHITE vs CRESTWOOD SC 2012 | 17 | MOORE PARK | Field 8 11v11 |
| 1171* | Sun 4/26 2:00pm | 14U/5S | CRESTWOOD SC 2012 vs CHICAGO EDGE B2012 COMPETITIVE | 26 | SHEPARD HIGH SCHOOL TURF | |
| 5307* | Sun 4/26 2:00pm |
13U/5S | ORLAND PARK STING FC 2013 SELECT 2 vs CRESTWOOD SC 2013/14 | 26 | SCHUSSLER PARK | Red Turf #2 |
| 3799 | Sat 5/2 3:00pm | 14U/5S | LTSC 2012 SELECT vs CRESTWOOD SC 2012 | 17 | WALKER PARK | 11v11 |
| 3272 | Sun 5/3 10:30am | 10U/5S2 | UESC - CHICAGOLAND 2016 SEL OP vs CRESTWOOD SC 2016 | 35 | COMMISSIONERS PARK (FRANKFORT) | |
| 3804* | Sun 5/3 1:30pm |
13U/5S | NAZ UNITED F.C. - 2013 ELITE vs CRESTWOOD SC 2013/14 | 17 | NAZARENE UNITED | |
| 4183 | Sat 5/9 10:00am | 14U/5S | CRESTWOOD SC 2012 vs CHICAGO BLAST 2012 GOLD | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 4212 | Sat 5/9 10:00am | 10U/5S2 | CRESTWOOD SC 2016 vs LEGACY SC 2016 SELECT | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 4647 | Sat 5/9 2:00pm | 13U/5S | MT GREENWOOD KNIGHTS SC 2014 vs CRESTWOOD SC 2013/14 | 32 | CHICAGO HIGH SCHOOL FOR AGRICULTURAL SCIENCES | |
| 327* | Sun 5/10 5:30pm |
10U/5S2 | ORLAND PARK STING FC 2016 SELECT vs CRESTWOOD SC 2016 | 26 | CENTENNIAL PARK (ORLAND PARK) | Field #7 (7v7) |
| 5148 | Sat 5/16 10:00am | 10U/5S2 | KORA FC 2016 ACADEMY vs CRESTWOOD SC 2016 | 26 | CENTENNIAL PARK (ORLAND PARK) | |
| 7073* | Sun 5/17 9:00am |
14U/5S | CRESTWOOD SC 2012 vs CSA 2012 B WHITE | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 3685* | Sun 5/24 2:00pm |
13U/5S | MWGFC 2013 PREMIER vs CRESTWOOD SC 2013/14 | 35 | KOSTNER PARK | |
| 6168* | Sat 5/30 10:00am | 10U/5S2 | CRESTWOOD SC 2016 vs LEGACY SC 2016 PREMIER | 26 | CRESTWOOD SOCCER CLUB | Shepard |
| 6111* | Sat 5/30 4:00pm | 13U/5S | CRESTWOOD SC 2013/14 vs MUSTANGS UNITED FC 2013 | 26 | SHEPARD HIGH SCHOOL TURF | |
| 6112* | Sat 5/30 6:00pm | 14U/5S | CRESTWOOD SC 2012 vs AYSO 300 UNITED 2012 WHITE | 26 | SHEPARD HIGH SCHOOL TURF | |
| 1170* | Sun 5/31 5:00pm |
13U/5S | CRESTWOOD SC 2013/14 vs KORA FC 2013 ELITE | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 7140* | Sat 6/6 9:00am |
10U/5S2 | CRESTWOOD SC 2016 vs CFA - MIDWEST WINGS 2016/17 | 26 | CRESTWOOD SOCCER CLUB | No Dogs Permitted |
| 7072* | Sat 6/6 10:00am | 13U/5S | CRESTWOOD SC 2013/14 vs MT GREENWOOD KNIGHTS SC 2014 | 26 | SHEPARD HIGH SCHOOL TURF |