| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 150* | Sat 9/12 8:00am | U14/4N | FC 1974 LIBERTYVILLE SELECT B2012/13 vs CHICAGO MAGIC 12/13 ELITE | 16 | LTSC FLD | Field 1 |
| 191* | Sat 9/12 8:00am |
U10/2N | CHICAGO MAGIC 16/17 PRE-ECNL vs SAA UNITED SC 16/17 BLACK | 16 | DANNY CUNNIFF | Small |
| 354* | Sat 9/12 9:00am |
U10/4N | FC 1974 LIBERTYVILLE ORANGE 2 B2016/17 vs CHICAGO MAGIC 16/17 ELITE | 16 | LTSC FLD | Field 17c |
| 223 | Sat 9/12 10:30am | U13/4N | CHICAGO MAGIC 13/14 ELITE vs IP-SKOMOR 13/14 PREMIER II | 16 | DANNY CUNNIFF | South Large |
| 465* | Sat 9/12 12:15pm | U11/4N | CHICAGO MAGIC 15/16 ELITE vs FC 1974 LIBERTYVILLE SELECT B2015/16 | 16 | HERITAGE PARK (WHEELING) | 9 |
| 568* | Sat 9/12 2:45pm | U12/4E2 | CHICAGO MAGIC 14/15 ELITE vs CHICAGO FC UNITED 14/15 PRE-ACADEMY II | 16 | HERITAGE PARK (WHEELING) | 9 |
| 2492* | Sun 9/13 8:00am |
U10/4N | NORRIDGE UNITED 16/17 PREMIER vs CHICAGO MAGIC 16/17 ELITE | 4 | DIVINE SAVIOR CHURCH | |
| 78* | Sun 9/13 10:00am |
U09/3NW | CHICAGO MAGIC 17/18 ELITE vs 60 UNITED - VHSC 17/18 ARGENTINA | 16 | DANNY CUNNIFF | Small |
| 827* | Sun 9/13 10:30am | U10/2N | IPROSKILLS 2016/17 NEON vs CHICAGO MAGIC 16/17 PRE-ECNL | 16 | ROGERS PARK | #2 |
| 1298 | Sat 9/19 2:00pm | U12/4E2 | ELITE STRIKERS 14/15 vs CHICAGO MAGIC 14/15 ELITE | 16 | FOX MEADOW | |
| 1779* | Wed 9/23 7:00pm |
U10/4N | CHICAGO MAGIC 16/17 ELITE vs FC-1 16/17 ELITE 2 | 16 | DANNY CUNNIFF | Small |
| 3571* | Sat 9/26 8:00am | U12/4E2 | CHICAGO MAGIC 14/15 ELITE vs OLYMPIACOS 14/15 PREMIER | 16 | HERITAGE PARK (WHEELING) | 8 |
| 1958* | Sat 9/26 8:30am | U11/4N | CHICAGO MAGIC 15/16 ELITE vs PEGASUS FC 15/16 BLACK | 16 | HERITAGE PARK (WHEELING) | 9 |
| 4302* | Sun 9/27 5:15pm |
U12/4E2 | CHICAGO MAGIC 14/15 ELITE vs CHICAGO PHOENIX FC 14/15 | 16 | HERITAGE PARK (WHEELING) | |
| 1111* | Wed 9/30 7:30pm |
U14/4N | CHICAGO MAGIC 12/13 ELITE vs FC MIRAGE 2012/13 RED | 16 | DANNY CUNNIFF | South |
| 1839* | Fri 10/2 7:30pm |
U14/4N | CHICAGO MAGIC 12/13 ELITE vs LASC 12/13 SELECT | 16 | DANNY CUNNIFF | South Large |
| 5519* | Sat 10/3 8:30am | U11/4N | LBR MUNDELEIN LIONS B15/16 vs CHICAGO MAGIC 15/16 ELITE | 35 | HERITAGE PARK (WHEELING) | |
| 2317* | Sat 10/3 9:00am | U10/2N | FCS EVANSTON 16/17 BOYS ORANGE vs CHICAGO MAGIC 16/17 PRE-ECNL | 3 | JAMES PARK | 1B |
| 2503 | Sat 10/3 10:45am | U14/4N | RUSH NORTH SHORE 12/13B BLUE vs CHICAGO MAGIC 12/13 ELITE | 16 | WILLOW HILL PARK | Field #3 |
| 2565* | Sat 10/3 1:00pm |
U10/4N | CHICAGO MAGIC 16/17 ELITE vs SPARTAN FC 16/17 ELITE | 16 | DANNY CUNNIFF | Small |
| 3710* | Sun 10/4 12:00pm rainout |
U10/4N | SCOUTS FC 2016/17 vs CHICAGO MAGIC 16/17 ELITE | 16 | LAKEWOOD GROVE PARK | |
| 2816 | Sun 10/4 2:15pm | U09/3NW | FCB 17/18 BLACK vs CHICAGO MAGIC 17/18 ELITE | 7 | SOUTH BARRINGTON COMMUNITY PARK | SB 1 North 7v7 |
| 5874* | Sun 10/4 3:00pm | U12/4E2 | CHICAGO PHOENIX FC 14/15 vs CHICAGO MAGIC 14/15 ELITE | 32 | TERRACE SCHOOL | |
| 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 4:00pm |
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 |
| 848* | Thu 10/15 7:15pm rainout |
U13/4N | CHICAGO MAGIC 13/14 ELITE vs NA - ROUND LAKE JUNIORS 13/14 SILVER | 16 | DANNY CUNNIFF | |
| 4090* | Fri 10/16 6:00pm |
U13/4N | FC 1974 LIBERTYVILLE PREMIER B2013/14 vs CHICAGO MAGIC 13/14 ELITE | 16 | LTSC FLD | Field 15 |
| 3785 | Sat 10/17 9:00am | U09/3NW | FC LAKE COUNTY 17/18 SELECT 1 vs CHICAGO MAGIC 17/18 ELITE | 16 | ALLEGHANY PARK | AH 2 |
| 4034* | Sat 10/17 9:00am |
U10/4N | CHICAGO MAGIC 16/17 ELITE vs HOTC 16/17 | 16 | DANNY CUNNIFF | Small |
| 4203* | Sat 10/17 1:15pm | U11/4N | CHICAGO MAGIC 15/16 ELITE vs SCOUTS FC 2015/16 | 16 | HERITAGE PARK (WHEELING) | 9 |
| 4032* | Sat 10/17 4:30pm |
U10/2N | CFYSC 16/17 PREMIER WHITE U10 vs CHICAGO MAGIC 16/17 PRE-ECNL | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 3350* | Sun 10/18 10:30am |
U10/2N | FORCE 16/17B ELITE BLUE vs CHICAGO MAGIC 16/17 PRE-ECNL | 14 | LIPPOLD PARK SOCCER COMPLEX | FIELD 6 |
| 1143* | Sun 10/18 11:30am |
U09/3NW | LASC 17/18 PREMIER vs CHICAGO MAGIC 17/18 ELITE | 16 | LAKE VILLA TOWNSHIP SOCCER COMPLEX | Field B 7v7 |
| 4254 | Sun 10/18 2:00pm | U14/4N | FC MIRAGE 2012/13 RED vs CHICAGO MAGIC 12/13 ELITE | 3 | WILLOW HILL PARK | 11v11 |
| 4542 | Sat 10/24 9:00am | U09/3NW | CHICAGO MAGIC 17/18 ELITE vs PALATINE CELTIC 17/18 BLACK | 16 | DANNY CUNNIFF | Small |
| 4693 | Sat 10/24 10:30am | U13/4N | CHICAGO MAGIC 13/14 ELITE vs RUSH NORTH SHORE 13/14B BLUE | 16 | DANNY CUNNIFF | South Large |
| 4587 | Sun 10/25 9:00am | U11/4N | NA - ROUND LAKE JUNIORS 2015/16 vs CHICAGO MAGIC 15/16 ELITE | 16 | PRAIRIE WALK PARK | |
| 4664* | Sun 10/25 10:00am |
U10/2N | CHICAGO MAGIC 16/17 PRE-ECNL vs ROCKFORD RAPTORS 16/17 - 1ST TEAM | 16 | DANNY CUNNIFF | Small field 1 |
| 4825* | Sun 10/25 11:00am |
U14/4N | CHICAGO MAGIC 12/13 ELITE vs FC 1974 LIBERTYVILLE SELECT B2012/13 | 16 | DANNY CUNNIFF | South Large |
| 1061* | Sun 10/25 12:30pm |
U10/4N | CHICAGO MAGIC 16/17 ELITE vs FC LAKE COUNTY 16/17 SELECT 2 | 16 | DANNY CUNNIFF | DANNY Cuniff Small |
| 2064* | Sun 10/25 2:00pm |
U12/4E2 | CHICAGO MAGIC 14/15 ELITE vs RUSH - WILMETTE WINGS 14/15B BLUE | 16 | HERITAGE PARK (WHEELING) | field #9 Grass |
| 5265* | Fri 10/30 6:00pm |
U09/3NW | CHICAGO MAGIC 17/18 ELITE vs SAA UNITED SC 17/18 BLACK I | 16 | DANNY CUNNIFF | Small |
| 5452* | Sat 10/31 8:30am |
U13/4N | CHICAGO MAGIC 13/14 ELITE vs NORRIDGE UNITED 13/14 SELECT | 16 | DANNY CUNNIFF | South Large |
| 5423 | Sat 10/31 10:15am | U10/2N | CHICAGO MAGIC 16/17 PRE-ECNL vs FC STARS 16/17 BLACK | 16 | DANNY CUNNIFF | Small |
| 5893* | Sat 10/31 10:30am |
U10/4N | NSFC 16/17 BLACK vs CHICAGO MAGIC 16/17 ELITE | 16 | NORTHCROFT PARK FIELD | |
| 5832* | Sat 10/31 1:30pm |
U11/4N | HAWTHORN WOODS ELITE 15/16 vs CHICAGO MAGIC 15/16 ELITE | 7 | HERITAGE OAKS | |
| 2601* | Sun 11/1 8:15am |
U11/4N | FC LAKE COUNTY 15/16 SELECT 1 vs CHICAGO MAGIC 15/16 ELITE | 16 | ALLEGHANY PARK | 4 |
| 5625 | Sun 11/1 12:00pm | U14/4N | NA - TREBOL F.C. 2012/13 vs CHICAGO MAGIC 12/13 ELITE | 16 | WAUKEGAN SPORTS PARK | |
| 3773* | Sat 11/7 10:30am |
U12/4E2 | CHICAGO FC UNITED 14/15 PRE-ACADEMY II vs CHICAGO MAGIC 14/15 ELITE | 16 | WILLOW PARK | 9v9 |
| 2651* | Sun 11/8 9:00am |
U12/4E2 | CHICAGO CELTIC SC 14/15 WHITE II vs CHICAGO MAGIC 14/15 ELITE | 4 | EDISON PARK ELEMENTARY |