| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 768* | Sat 9/6 12:00pm |
10U/1 | CHICAGO RAIDERS 16/17 vs RUSH - WILMETTE WINGS 2016 PREMIER VAPOR | 7 | UDALL PARK | |
| 635* | Sun 9/7 2:00pm | 11U/1S | ORLAND PARK STING FC 2015 PREMIER vs CHICAGO RAIDERS 2016 | 26 | SCHUSSLER PARK | Blue Turf #1 |
| 1552* | Sat 9/13 3:00pm | 10U/1 | RUSH - WILMETTE WINGS 2016 PREMIER PHANTOM vs CHICAGO RAIDERS 16/17 | 16 | WILMETTE COMMUNITY PLAYFIELD | Field #4 |
| 2574 | Sat 9/20 5:00pm | 11U/1S | BERBER CITY FC 2015 BLUE vs CHICAGO RAIDERS 2016 | 32 | DUNBAR SOCCER COMPLEX | |
| 2020* | Sun 9/21 8:00pm |
10U/1 | BARCA ACADEMY CHICAGO 2016 BLAU vs CHICAGO RAIDERS 16/17 | 7 | OLYMPIC PARK FIELD | Field 8 |
| 3412* | Sun 9/28 4:00pm |
10U/1 | CHICAGO RAIDERS 16/17 vs CFA - COSMOS FC 2016 | 7 | UDALL PARK | |
| 3565* | Sat 10/4 9:00am | 11U/1S | CHICAGO RAIDERS 2016 vs WCOB FC 2015 SELECT | 7 | SANDERS FIELD | |
| 4398* | Sun 10/5 10:00am |
11U/1S | CHICAGO RAIDERS 2016 vs CHICAGO EMPIRE FC 2015 PRE EA | 7 | SANDERS FIELD | |
| 3660* | Sun 10/5 3:30pm |
10U/1 | WHEATON UNITED 2016 ACADEMY RED vs CHICAGO RAIDERS 16/17 | 17 | KELLY PARK | |
| 5265* | Sat 10/18 9:00am | 11U/1S | CHICAGO RAIDERS 2016 vs ECLIPSE 2015 DARIEN BOYS | 7 | SANDERS FIELD | |
| 5788 | Sat 10/18 1:30pm | 10U/1 | WCOB FC 2016/17 SELECT vs CHICAGO RAIDERS 16/17 | 17 | CENTRAL PARK NORTH (OAK BROOK) | Field 8 |
| 6112 | Sat 10/25 9:00am | 11U/1S | GALAXY 2015 SELECT BLUE vs CHICAGO RAIDERS 2016 | 6 | JUST FOR KICKS SOCCER FACILITY | Medium - 1 |
| 6861 | Sat 10/25 4:00pm | 10U/1 | CHICAGO RAIDERS 16/17 vs CHICAGO EMPIRE FC 2016 GOLD 1 | 7 | UDALL PARK | |
| 5134* | Sat 11/1 9:00am |
10U/1 | CHICAGO RAIDERS 16/17 vs ORLAND PARK STING FC 2016 PREMIER | 7 | UDALL PARK | |
| 920* | Sat 11/1 3:00pm |
11U/1S | CHICAGO RAIDERS 2016 vs AAC EAGLES CHICAGO 2015 WHITE | 7 | SANDERS FIELD | |
| 3356* | Sun 11/2 12:00pm |
11U/1S | LTSC 2015 SELECT WHITE vs CHICAGO RAIDERS 2016 | 17 | WALKER PARK | 9v9 |