| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 18 | Sat 9/12 8:00am | U07-4V4/S2 | GESC 19/20 vs MWGFC 19/20 ELITE | 66 | PRAIRIE PARK (CHICAGO) | |
| 459 | Sat 9/12 1:00pm | U10/5S2 | MWGFC 16/17 ELITE vs ORLAND PARK STING FC 16/17 ELITE | 35 | KOSTNER PARK | |
| 664* | Sat 9/12 4:00pm | U14/5S | CRESTWOOD SC 12/13 vs MWGFC 12/13 PREMIER | 26 | SHEPARD HIGH SCHOOL TURF | |
| 5721* | Sun 9/13 10:30am |
U10/5S2 | UESC - CHICAGOLAND 16/17B SELECT vs MWGFC 16/17 ELITE | 35 | COMMISSIONERS PARK (FRANKFORT) | |
| 3016* | Sun 9/13 3:00pm |
U13/5S | MILLENNIUM SA 13/14 WHITE vs MWGFC 13/14 ELITE | 8 | CROWN POINT SPORTSPLEX | Turf B |
| 739* | Sun 9/13 4:45pm |
U10/5S2 | MILLENNIUM SA 16/17 BLACK vs MWGFC 16/17 ELITE | 8 | CROWN POINT SPORTSPLEX | Turf B - 7v7 |
| 2020* | Tue 9/22 5:30pm |
U09/5S | TINLEY PARK BOBCATS 17/18 BLACK vs MWGFC 17/18 PREMIER | 26 | VOLUNTEER PARK (TINLEY PARK) | |
| 5111* | Wed 9/23 6:00pm |
U14/5S | MWGFC 12/13 PREMIER vs UESC - CHICAGOLAND 12/13B SELECT BB | 35 | KOSTNER PARK | |
| 858* | Sat 9/26 11:00am |
U08-7V7/5S | MWGFC 18/19 ELITE vs CHICAGO EDGE B18/19 COMPETITIVE | 35 | BREMEN HEIGHTS PARK | |
| 1948* | Sat 9/26 12:00pm |
U10/5S2 | MWGFC 16/17 ELITE vs MILLENNIUM SA 16/17 BLACK | 35 | KOSTNER PARK | |
| 2035* | Sat 9/26 2:00pm | U13/5S | CHICAGO PRO SA 13/14 M'DAKHAN vs MWGFC 13/14 ELITE | 35 | MARTIN PARK | 11V11 |
| 1946* | Sat 9/26 5:00pm |
U07-4V4/S2 | CHICAGO EMPIRE FC 19/20 INTER MILAN vs MWGFC 19/20 ELITE | 66 | OAK BROOK POLO FIELDS | H 5v5 |
| 121* | Sun 9/27 1:30pm |
U08-7V7/5S | MWGFC 18/19 ELITE vs NAZ UNITED F.C. - 18/19 ELITE | 35 | BREMEN HEIGHTS PARK | |
| 1043* | Sun 9/27 3:00pm |
U07-4V4/S2 | MWGFC 19/20 ELITE vs UESC - CHICAGOLAND 19/20B SELECT | 66 | BREMEN HEIGHTS PARK | |
| 1950* | Fri 10/2 6:00pm rainout |
U14/5S | KORA FC 12/13 ELITE vs MWGFC 12/13 PREMIER | 26 | CENTENNIAL PARK (ORLAND PARK) | |
| 2408* | Sat 10/3 11:00am |
U10/5S2 | TINLEY PARK BOBCATS 16/17 BLACK vs MWGFC 16/17 ELITE | 26 | VOLUNTEER PARK (TINLEY PARK) | |
| 2551* | Sat 10/3 2:00pm |
U07-4V4/S2 | MWGFC 19/20 ELITE vs CHICAGO EMPIRE FC 19/20 BARCELONA | 66 | BREMEN HEIGHTS PARK | |
| 4195* | Sun 10/4 11:00am |
U10/5S2 | MWGFC 16/17 ELITE vs UESC - CHICAGOLAND 16/17B SELECT | 35 | KOSTNER PARK | |
| 2863 | Sun 10/4 3:00pm | U08-7V7/5S | TESC 18/19 SELECT BLACK vs MWGFC 18/19 ELITE | 17 | CONRAD FISCHER PARK | 7 VS 7 |
| 3130* | Thu 10/15 6:30pm rainout |
U07-4V4/S2 | ACADEMIA ATLAS FC CHICAGO 19/20 ZORROS vs MWGFC 19/20 ELITE | 32 | VITTUM PARK | |
| 4009* | Sat 10/17 11:00am | U09/5S | CHICAGO PRO SA 17/18 OASIS vs MWGFC 17/18 PREMIER | 35 | MARTIN PARK | 7x7 |
| 4015 | Sat 10/17 11:00am rainout |
U07-4V4/S2 | MWGFC 19/20 ELITE vs GESC 19/20 | 66 | BREMEN HEIGHTS PARK | |
| 4237 | Sat 10/17 1:30pm | U08-7V7/5S | NAZ UNITED F.C. - 18/19 ELITE vs MWGFC 18/19 ELITE | 17 | NAZARENE UNITED | |
| 4450 | Sat 10/17 5:00pm | U13/5S | CHICAGO KICS FC 13/14 BLUE SOUTH vs MWGFC 13/14 ELITE | 25 | EVERGREEN PARK HIGH SCHOOL | 11 v 11 |
| 650* | Sun 10/18 10:00am |
U13/5S | LEGACY SC 13/14 SELECT vs MWGFC 13/14 ELITE | 26 | SPENCER SCHOOL CAMPUS | Field 3 - 11v11 |
| 4166* | Sun 10/18 1:00pm | U14/5S | MUSTANGS UNITED FC 12/13 vs MWGFC 12/13 PREMIER | 17 | RICE PARK | |
| 3285* | Sun 10/18 4:00pm |
U08-7V7/5S | CHICAGO EDGE B18/19 SELECT vs MWGFC 18/19 ELITE | 12 | PRIORY PARK | West - 7v7 |
| 4595* | Sat 10/24 9:00am | U08-7V7/5S | MWGFC 18/19 ELITE vs CHICAGO PRO SA 18/19 P.A.C | 35 | BREMEN HEIGHTS PARK | 11500 beloit ave in |
| 4862* | Sat 10/24 12:00pm | U09/5S | MWGFC 17/18 PREMIER vs KORA FC 17/18 ELITE | 35 | KOSTNER PARK | 11500 beloit ave in, |
| 5018 | Sat 10/24 2:00pm | U13/5S | MWGFC 13/14 ELITE vs ORLAND PARK STING FC 13/14 ELITE 2 | 35 | KOSTNER PARK | |
| 5172* | Sat 10/24 5:00pm | U07-4V4/S2 | EVERGREEN UNITED FC 19/20 vs MWGFC 19/20 ELITE | 66 | NORTHEAST ELEMENTARY SCHOOL | |
| 3629* | Sun 10/25 9:30am |
U14/5S | MWGFC 12/13 PREMIER vs NWI LIONS UTD 12/13 YELLOW II | 35 | KOSTNER PARK | |
| 4990* | Sun 10/25 4:30pm |
U10/5S2 | ORLAND PARK STING FC 16/17 ELITE vs MWGFC 16/17 ELITE | 26 | EAGLE RIDGE II PARK | |
| 2255* | Thu 10/29 5:00pm |
U09/5S | RANGERS SOCCER ACADEMY 17/18 vs MWGFC 17/18 PREMIER | 35 | ALTMAN PARK | |
| 5327 | Sat 10/31 9:00am | U08-7V7/5S | MWGFC 18/19 ELITE vs CHICAGO EDGE B18/19 SELECT | 35 | BREMEN HEIGHTS PARK | |
| 3385* | Sat 10/31 10:00am |
U09/5S | MWGFC 17/18 PREMIER vs LEGACY SC 17/18 SELECT | 35 | KOSTNER PARK | |
| 5522* | Sat 10/31 11:30am |
U07-4V4/S2 | MWGFC 19/20 ELITE vs CHICAGO EMPIRE FC 19/20 INTER MILAN | 66 | BREMEN HEIGHTS PARK | |
| 5788 | Sat 10/31 2:00pm | U13/5S | MWGFC 13/14 ELITE vs CHICAGO KICS FC 13/14 BLUE SOUTH | 35 | KOSTNER PARK | |
| 5629* | Sun 11/1 10:00am |
U09/5S | MWGFC 17/18 PREMIER vs UESC-CHICAGO SOUTH SHORE 17/18 | 35 | KOSTNER PARK | |
| 3459* | Sun 11/1 11:00am |
U10/5S2 | MWGFC 16/17 ELITE vs TINLEY PARK BOBCATS 16/17 BLACK | 35 | KOSTNER PARK | |
| 2810* | Sun 11/1 1:00pm |
U13/5S | MWGFC 13/14 ELITE vs UESC-CHICAGO SOUTH SHORE 13/14 | 35 | KOSTNER PARK | |
| 2911* | Sun 11/1 3:00pm |
U14/5S | MWGFC 12/13 PREMIER vs ORLAND PARK STING FC 12/13 ELITE 2 | 35 | KOSTNER PARK | |
| 64* | Sat 11/7 11:00am |
U09/5S | MT GREENWOOD KNIGHTS SC 17/18 vs MWGFC 17/18 PREMIER | 32 | MT GREENWOOD PARK | |
| 2875* | Sat 11/7 12:00pm | U08-7V7/5S | EVERGREEN UNITED FC 18/19 vs MWGFC 18/19 ELITE | 17 | NORTHEAST ELEMENTARY SCHOOL | |
| 865* | Sat 11/7 3:00pm |
U14/5S | NWI LIONS UTD 12/13 YELLOW II vs MWGFC 12/13 PREMIER | 8 | NWI CHESTERTON SOCCER FIELDS | 11v11 - Field #1 |
| 1148* | Sun 11/8 12:00pm |
U09/5S | MWGFC 17/18 PREMIER vs UESC - CHICAGOLAND 17/18B SELECT | 35 | KOSTNER PARK | |
| 5884* | Sun 11/8 2:00pm |
U14/5S | MWGFC 12/13 PREMIER vs MUSTANGS UNITED FC 12/13 | 35 | KOSTNER PARK | |
| 1312* | Sun 11/8 3:30pm |
U13/5S | MWGFC 13/14 ELITE vs UESC - CHICAGOLAND 13/14B SELECT | 35 | KOSTNER PARK |