| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 846* | Sun 9/7 10:00am |
8U-5V5/5S2 | RANGERS SOCCER ACADEMY 2018 vs MWGFC 2018 PREMIER | 33 | ALTMAN PARK | |
| 410* | Sun 9/7 2:00pm | 9U/5S | MUSTANGS UNITED FC 2017 vs MWGFC 2017 ELITE | 17 | MARTIN PARK | |
| 5394* | Sat 9/13 9:00am rainout |
7U-4V4/S | MWGFC 2019 ELITE vs INDIANA ELITE CHICAGO 2020 | 66 | BREMEN HEIGHTS PARK | |
| 1369 | Sat 9/13 1:00pm | 13U/5SE | CHICAGO EMPIRE FC SOUTH 13/14 BLUE vs MWGFC 2013 PREMIER | 33 | CAESAR PARK | 11v11 |
| 1165 | Sun 9/14 11:00am | 8U-5V5/5S2 | CHICAGO BLAST 2018 RED vs MWGFC 2018 PREMIER | 17 | BELLERIVE PARK | |
| 6580* | Sun 9/14 4:00pm |
13U/5SE | MWGFC 2013 PREMIER vs ACADEMIA ATLAS 2013/14 RED | 33 | KOSTNER PARK | |
| 518* | Sun 9/21 1:00pm |
13U/5SE | MWGFC 2013 PREMIER vs MUSTANGS UNITED FC 2013 | 33 | KOSTNER PARK | |
| 2721* | Sat 9/27 10:00am |
7U-4V4/S | MT GREENWOOD KNIGHTS SC 19/20 vs MWGFC 2019 ELITE | 66 | MT GREENWOOD PARK | 1 |
| 2812 | Sat 9/27 10:00am | 9U/5S | MT GREENWOOD KNIGHTS SC 2017 vs MWGFC 2017 ELITE | 32 | MT GREENWOOD PARK | 1 |
| 2811 | Sat 9/27 10:00am | 8U-5V5/5S2 | MT GREENWOOD KNIGHTS SC 18 vs MWGFC 2018 PREMIER | 32 | MT GREENWOOD PARK | 1 |
| 1854* | Sun 9/28 10:00am |
8U-5V5/5S2 | MWGFC 2018 PREMIER vs ORLAND PARK STING FC 2018 ELITE | 33 | BREMEN HEIGHTS PARK | |
| 181* | Sun 9/28 11:00am |
7U-4V4/S | MWGFC 2019 ELITE vs ORLAND PARK STING FC 2019 | 66 | BREMEN HEIGHTS PARK | |
| 1490* | Sun 9/28 4:00pm |
9U/5S | LEGACY SC 2017 vs MWGFC 2017 ELITE | 26 | SPENCER SCHOOL CAMPUS | Field 12 - 7v7 |
| 3591* | Sun 10/5 9:00am | 7U-4V4/S | GESC 2019 CHICHO CUEVAS vs MWGFC 2019 ELITE | 66 | PRAIRIE PARK (CHICAGO) | 4v4 |
| 3927* | Sun 10/5 10:00am | 9U/5S | MWGFC 2017 ELITE vs CHICAGO CITY 2017 SOUTH I | 33 | KOSTNER PARK | |
| 1067* | Sun 10/5 3:00pm |
7U-4V4/S | MWGFC 2019 ELITE vs CHICAGO EMPIRE FC 2019 WHITE | 66 | BREMEN HEIGHTS PARK | |
| 3625* | Sun 10/5 4:00pm |
8U-5V5/5S2 | MWGFC 2018 PREMIER vs CHICAGO KICS 2018 WHITE (CITY) | 33 | BREMEN HEIGHTS PARK | |
| 4450* | Sun 10/12 9:00am |
8U-5V5/5S2 | MWGFC 2018 PREMIER vs LTSC 2018/19 TRAVEL BLUE | 33 | BREMEN HEIGHTS PARK | |
| 6231* | Sun 10/12 12:00pm |
7U-4V4/S | MWGFC 2019 ELITE vs GESC 2019 CHICHO CUEVAS | 66 | BREMEN HEIGHTS PARK | |
| 2179* | Sun 10/12 12:00pm |
9U/5S | MWGFC 2017 ELITE vs CHICAGO UNITED 2017 STORM | 33 | KOSTNER PARK | |
| 3149* | Sun 10/12 2:00pm |
13U/5SE | MWGFC 2013 PREMIER vs CHICAGO UNITED 2013 TITANS | 33 | KOSTNER PARK | |
| 6500* | Tue 10/28 5:00pm |
9U/5S | ORLAND PARK STING FC 2017 ELITE vs MWGFC 2017 ELITE | 26 | EAGLE RIDGE II PARK | 7v7 |
| 5838* | Tue 10/28 7:00pm |
13U/5SE | ORLAND PARK STING FC 2013 SELECT 2 vs MWGFC 2013 PREMIER | 26 | SCHUSSLER PARK | |
| 5319* | Thu 10/30 7:00pm | 8U-5V5/5S2 | ACADEMIA ATLAS FC 2018 SELECT vs MWGFC 2018 PREMIER | 32 | VITTUM PARK | |
| 4779* | Sat 11/1 11:00am |
9U/5S | MWGFC 2017 ELITE vs WINDY CITY PRIDE 2017 | 33 | KOSTNER PARK | |
| 2145* | Sat 11/1 12:30pm |
13U/5SE | CRESTWOOD SC 2013/14 vs MWGFC 2013 PREMIER | 33 | SHEPARD HIGH SCHOOL TURF | |
| 5621* | Sat 11/1 3:30pm |
9U/5S | MWGFC 2017 ELITE vs PSG ACADEMY LEMONT 2017 | 33 | KOSTNER PARK | 1 |
| 4886* | Sat 11/1 4:30pm |
13U/5SE | MWGFC 2013 PREMIER vs KORA FC 2013 ELITE | 33 | KOSTNER PARK | |
| 6249* | Sun 11/2 9:00am |
8U-5V5/5S2 | ORLAND PARK STING FC 2018 ELITE vs MWGFC 2018 PREMIER | 26 | CENTENNIAL PARK (ORLAND PARK) | Field #6 (5v5) |
| 4466* | Sun 11/2 10:00am |
7U-4V4/S | ORLAND PARK STING FC 2019 vs MWGFC 2019 ELITE | 66 | CENTENNIAL PARK (ORLAND PARK) | Field #6 |
| 2023* | Sun 11/2 1:30pm |
7U-4V4/S | CHICAGO EMPIRE FC 2019 WHITE vs MWGFC 2019 ELITE | 66 | OAK BROOK POLO FIELDS | H 5v5 |
| 2099 | Wed 12/31 11:45am | 13U/5SE | WINDY CITY PRIDE 2013 vs MWGFC 2013 PREMIER | 33 | HICKORY CREEK MIDDLE SCHOOL |