| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 879* | Sat 4/12 12:00pm | 18U/2 | WINDY CITY FC 2007 vs FSC 2007 BLACK | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 1800* | Sat 4/12 1:00pm | 8U-7V7/5NW | FORCE 2017B PREMIER WHITE vs WINDY CITY FC 2017 | 1 | LIPPOLD PARK SOCCER COMPLEX | FIELD 7 |
| 1903* | Sat 4/12 5:00pm | 11U/4NE | LEO SOCCER SCHOOL 2014 vs WINDY CITY FC 2014 | 7 | HERITAGE PARK (WHEELING) | #9 |
| 144* | Sun 4/13 9:00am | 11U/4NE | WINDY CITY FC 2014 vs JOM SC 2014 | 7 | HERITAGE PARK (WHEELING) | FIELD 8 |
| 1448 | Sun 4/13 12:00pm | 9U/4NW2 | WINDY CITY FC 2016 vs ELA 2016 ELITE PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 1449* | Sun 4/13 2:00pm |
13U/5N | WINDY CITY FC 2012 vs LIBERTYVILLE FC 1974-12C-PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 1862* | Sun 4/13 4:00pm | 16U/3N | WINDY CITY FC 2009 vs FORCE 2009B ELITE POOL | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 2367* | Sat 4/19 12:00pm | 14U/4N | LIBERTYVILLE FC 1974-11C-PREMIER vs WINDY CITY FC 2011 | 1 | LTSC FLD | Field 1 |
| 2256* | Sat 4/19 3:35pm |
13U/5N | LASC 2013 PREMIER vs WINDY CITY FC 2012 | 16 | LAKE VILLA TOWNSHIP SOCCER COMPLEX | Field E - 11v11 |
| 973* | Fri 4/25 6:30pm |
18U/2 | IPROSKILLS 2007/2008 vs WINDY CITY FC 2007 | 16 | LERNER PARK | |
| 2976 | Sat 4/26 9:00am | 11U/4NE | ELITE S.C. 2014 RED vs WINDY CITY FC 2014 | 7 | HERITAGE PARK (WHEELING) | #9 9v9 |
| 3384* | Sat 4/26 12:00pm | 12U/3N | WINDY CITY FC 2013 vs HAWTHORN WOODS ELITE 2013 BLACK | 7 | HERITAGE PARK (WHEELING) | FIELD 8 |
| 3710 | Sat 4/26 3:00pm | 9U/4NW2 | FCX 2016 BLACK PREMIER vs WINDY CITY FC 2016 | 7 | RON BEESE PARK | RB 2 |
| 2198* | Sun 4/27 9:00am |
8U-7V7/5NW | WINDY CITY FC 2017 vs PALATINE CELTIC 2017 GREEN | 7 | HERITAGE PARK (WHEELING) | Field 7 |
| 3385 | Sun 4/27 12:00pm | 13U/5N | WINDY CITY FC 2012 vs ELA 2012 ELITE SELECT | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 3846* | Sun 4/27 4:00pm | 16U/3N | WINDY CITY FC 2009 vs LASC 2009/10 PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 920* | Sat 5/3 10:00am | 9U/4NW2 | PALATINE CELTIC 2016 GREEN vs WINDY CITY FC 2016 | 7 | CELTIC PARK FIELD | Celtic #4 North |
| 4143 | Sat 5/3 10:30am | 11U/4NE | FC-1 ACADEMY 2015 ELITE vs WINDY CITY FC 2014 | 16 | COMMUNITY PARK WEST (GLENVIEW) | 2 - (9 v 9)) |
| 4433 | Sat 5/3 1:00pm | 13U/5N | NA - ROUND LAKE JUNIORS 2012 vs WINDY CITY FC 2012 | 16 | ROUND LAKE AREA PARK DISTRICT (SPORTS CENTER) | |
| 5631* | Sat 5/3 2:00pm |
16U/3N | FC LAKE COUNTY 2009 ELITE POOL vs WINDY CITY FC 2009 | 1 | ALLEGHANY PARK | AH 11 |
| 4362* | Sat 5/3 4:30pm |
12U/3N | FORCE 2013B ELITE WHITE vs WINDY CITY FC 2013 | 1 | TOMASO | 5 |
| 664* | Sat 5/3 6:00pm |
14U/4N | NSFC 2011 BLACK vs WINDY CITY FC 2011 | 16 | LAKE FOREST HIGH SCHOOL WEST CAMPUS | |
| 4186* | Sun 5/4 9:00am |
16U/3N | FORCE 2009B ELITE POOL vs WINDY CITY FC 2009 | 1 | LIPPOLD PARK SOCCER COMPLEX | FIELD 2 |
| 4354 | Sun 5/4 12:00pm | 9U/4NW2 | WINDY CITY FC 2016 vs GREEN WHITE 2016 GRUN | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 4229* | Sun 5/4 5:45pm |
14U/4N | REAL MADRID ROUND LAKE FC 2011 vs WINDY CITY FC 2011 | 16 | ROUND LAKE AREA PARK DISTRICT (SPORTS CENTER) | |
| 2101* | Sun 5/4 6:00pm |
12U/3N | BARCA ACADEMY CHICAGO 2013 GROC vs WINDY CITY FC 2013 | 7 | OLYMPIC PARK FIELD | Field 8 |
| 2140* | Fri 5/9 6:00pm |
9U/4NW2 | NA - EAGLES LAKE COUNTY FC 2016 vs WINDY CITY FC 2016 | 16 | TOWNLINE PARK | |
| 4931 | Sat 5/10 9:00am | 11U/4NE | IEFC WOLFPACK FC 2014/15 vs WINDY CITY FC 2014 | 12 | HARRIET E SAYRE ELEMENTARY SCHOOL | |
| 6022* | Sat 5/10 10:00am | 13U/5N | LIBERTYVILLE FC 1974-12C-PREMIER vs WINDY CITY FC 2012 | 1 | LTSC FLD | Field 1 |
| 5309* | Sat 5/10 12:00pm | 12U/3N | LIBERTYVILLE FC 1974-13B-SELECT 1 vs WINDY CITY FC 2013 | 1 | LTSC FLD | 2 |
| 5018* | Sat 5/10 2:00pm |
8U-7V7/5NW | HUSSARS UNITED 2017 vs WINDY CITY FC 2017 | 35 | ALGONQUIN MIDDLE SCHOOL (DES PLAINES) | |
| 6683* | Sat 5/10 5:00pm |
18U/2 | WINDY CITY FC 2007 vs OPRF ALLIANCE 2007 | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 100* | Sat 5/10 5:45pm |
13U/5N | PEGASUS FC/1974 (2012) WHITE vs WINDY CITY FC 2012 | 16 | CLAVEY PARK | Large |
| 6682* | Sat 5/17 8:30am |
16U/3N | WINDY CITY FC 2009 vs CHICAGO MAGIC 2009 RL ELITE | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 5979* | Sat 5/17 11:15am |
11U/4NE | WINDY CITY FC 2014 vs CELTIC FC CHICAGO 2014 GREEN | 7 | HERITAGE PARK (WHEELING) | FIELD 9 |
| 6237 | Sat 5/17 12:00pm | 12U/3N | FC LAKE COUNTY 2013 SELECT 2 vs WINDY CITY FC 2013 | 1 | ALLEGHANY PARK | AH 3 |
| 7204* | Sat 5/17 2:00pm |
9U/4NW2 | FC LAKE COUNTY 2016 SELECT 2 vs WINDY CITY FC 2016 | 1 | ALLEGHANY PARK | AH 2 |
| 6510* | Sat 5/17 2:30pm | 14U/4N | MUNDELEIN LIONS 2011 vs WINDY CITY FC 2011 | 16 | FREMONT SCHOOL (NO PETS) | 3 |
| 4403* | Sat 5/17 4:40pm |
8U-7V7/5NW | CARY DEFENDERS 2017 vs WINDY CITY FC 2017 | 1 | CARY GROVE PARK | EAST |
| 3432* | Sat 5/17 6:00pm |
18U/2 | CHICAGO INTER KCSA 2007 BLACK vs WINDY CITY FC 2007 | 32 | CHICAGO INTER SOCCER COMPLEX | A |
| 2810* | Sun 5/18 9:00am |
18U/2 | WINDY CITY FC 2007 vs KORA FC 2007 | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 6288* | Sun 5/18 9:00am |
9U/4NW2 | WINDY CITY FC 2016 vs CARY DEFENDERS 2016 | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 6115 | Sun 5/18 10:30am | 8U-7V7/5NW | WINDY CITY FC 2017 vs RISING TIDE 2017 | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 5310* | Sun 5/18 12:30pm |
13U/5N | WINDY CITY FC 2012 vs PEGASUS FC/1974 (2012) WHITE | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 2839* | Sun 5/18 1:30pm | 16U/3N | 60 UNITED - LFSA 2009 BLUE vs WINDY CITY FC 2009 | 1 | DEERPATH COMMUNITY PARK (LAKE FOREST) | |
| 1007* | Sun 5/18 4:30pm |
12U/3N | CHICAGO MAGIC 2013 ELITE vs WINDY CITY FC 2013 | 16 | LINCOLN SCHOOL SOCCER FIELD | |
| 4285* | Fri 5/23 6:15pm |
18U/2 | CHICAGO PHOENIX FC 2007 vs WINDY CITY FC 2007 | 32 | MAINE WEST HIGH SCHOOL | |
| 7274 | Sat 5/31 12:00pm | 12U/3N | WINDY CITY FC 2013 vs FC LAKE COUNTY 2013 SELECT 2 | 7 | HERITAGE PARK (WHEELING) | FIELD 9 |
| 7360 | Sat 5/31 1:00pm | 14U/4N | WINDY CITY FC 2011 vs LIBERTYVILLE FC 1974-11C-PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 7275* | Sat 5/31 2:45pm |
13U/5N | WINDY CITY FC 2012 vs LASC 2013 PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 7705 | Sat 5/31 4:00pm | 18U/2 | WINDY CITY FC 2007 vs UESC - FC LAKESHORE 2007/08 PREMIER | 7 | HERITAGE PARK (WHEELING) | FIELD 11 |
| 1536* | Sun 6/1 9:00am |
14U/4N | WINDY CITY FC 2011 vs CHICAGO MAGIC 2011 CUP | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 7078 | Sun 6/1 10:30am | 8U-7V7/5NW | WINDY CITY FC 2017 vs SAA UNITED SC 2017 RED | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 2080* | Sun 6/1 12:00pm |
11U/4NE | WINDY CITY FC 2014 vs PALATINE CELTIC 2014 GREEN | 7 | HERITAGE PARK (WHEELING) | FIELD 9 |
| 459* | Sun 6/1 12:00pm |
12U/3N | WINDY CITY FC 2013 vs IP-ARLINGTON ACES 2013 BLUE | 7 | HERITAGE PARK (WHEELING) | FIELD 9 |
| 5308* | Sun 6/1 3:30pm |
9U/4NW2 | WINDY CITY FC 2016 vs CHICAGO INFERNO 2016 PREMIER 1 | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 6920* | Mon 6/2 6:00pm |
11U/4NE | WINDY CITY FC 2014 vs IP-ARLINGTON ACES 2014 BLUE | 7 | HERITAGE PARK (WHEELING) | FIELD 9 |
| 3482* | Sat 6/7 9:00am |
14U/4N | WINDY CITY FC 2011 vs FC-1 ACADEMY 2011 SELECT BLUE | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 7704* | Sat 6/7 12:00pm |
16U/3N | WINDY CITY FC 2009 vs FC LAKE COUNTY 2009 ELITE POOL | 7 | HERITAGE PARK (WHEELING) | FIELD 11 |
| 5412* | Sat 6/7 5:30pm |
14U/4N | WINDY CITY FC 2011 vs NSFC 2011 BLACK | 7 | HERITAGE PARK (WHEELING) | FIELD 10 |
| 1411* | Sun 6/8 12:00pm | 16U/3N | LIBERTYVILLE FC 1974-09B-SELECT 2 vs WINDY CITY FC 2009 | 1 | LTSC FLD | Field 9 |
| 271* | Sun 6/8 12:00pm |
8U-7V7/5NW | WINDY CITY FC 2017 vs ELITE S.C. 2017/18 RED | 7 | HERITAGE PARK (WHEELING) | FIELD 7 |
| 3875* | Wed 12/31 9:00am |
8U-7V7/5NW | BARCA ACADEMY CHICAGO 2017 BLAU vs WINDY CITY FC 2017 | 7 | OLYMPIC PARK FIELD | Field 7 |
| 5819* | Wed 12/31 5:45pm |
18U/2 | CHICAGO CITY 2007/2008 I vs WINDY CITY FC 2007 | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | 11v11 |