| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 1689* | Fri 10/9 6:30pm |
U13/4N | CHICAGO MAGIC 13/14 ELITE vs PEGASUS FC 13/14 BLACK | 16 | DANNY CUNNIFF | South field |
| 3121 | Sat 10/10 9:00am | U13/4N | IP-NUFC 13/14 BLACK vs CHICAGO MAGIC 13/14 ELITE | 14 | MCHENRY TOWNSHIP | #1 (U13-U18) |
| 3358 | Sat 10/10 12:00pm | U14/4N | CHICAGO MAGIC 12/13 ELITE vs NA - TREBOL F.C. 2012/13 | 16 | DANNY CUNNIFF | South Large |
| 3217* | Sun 10/11 9:00am |
U09/3NW | FORCE 17/18B ELITE WHITE vs CHICAGO MAGIC 17/18 ELITE | 14 | LIPPOLD PARK SOCCER COMPLEX | FIELD 6 |
| 2604* | Sun 10/11 11:30am | U13/4N | FC LAKE COUNTY 13/14 SELECT 1 vs CHICAGO MAGIC 13/14 ELITE | 16 | HUNT CLUB PARK | HC 1 |
| 1561* | Sun 10/11 1:00pm |
U09/3NW | CHICAGO MAGIC 17/18 ELITE vs CHICAGO CITY ELGIN 17/18 | 16 | DANNY CUNNIFF | Small |
| 3466* | Sun 10/11 4:30pm | U11/4N | CHICAGO MAGIC 15/16 ELITE vs NSFC 15/16 BLACK | 16 | HERITAGE PARK (WHEELING) | 8 |
| 1655* | Tue 10/13 7:00pm |
U10/2N | CHICAGO MAGIC 16/17 PRE-ECNL vs PEGASUS FC 16/17 RED | 16 | DANNY CUNNIFF | Small |