| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 6352* | Sat 10/25 9:00am |
14U/3CITY | IEFC WOLFPACK FC 2012/13 vs CHICAGO CITY 2012 I | 12 | HARRIET E SAYRE ELEMENTARY SCHOOL | |
| 6159* | Sat 10/25 9:00am | 9U/3E | SAA UNITED SC 2017 BLACK vs CHICAGO CITY 2017 ACADEMY I | 7 | OLYMPIC PARK FIELD | 8A |
| 6091* | Sat 10/25 9:00am | 8U-5V5/5S1 | CHICAGO CITY 2018 SOUTH I vs UESC - CHICAGOLAND 2018 SEL BB | 26 | EAGLE RIDGE II PARK | |
| 6900* | Sat 10/25 9:00am |
10U/5CITY2 | CHICAGO CELTIC SC 2016 WHITE vs CHICAGO CITY 2016 V | 4 | HITCH ELEMENTARY SCHOOL | |
| 6157* | Sat 10/25 9:00am | 13U/4NW | ROCKFORD RAPTORS 2013 NAVY vs CHICAGO CITY PUMAS SC 2013 BLUE | 9 | SPORTSCORE 2 & SPORTSCORE 1 (WTNG ON PD) | 218 |
| 6190 | Sat 10/25 9:15am | 13U/4CITY | CHICAGO CITY 2013 LOOP I vs BERBER CITY FC 2013 | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | |
| 6099* | Sat 10/25 9:30am | 7U-4V4/W | EGSC 2019 PREMIER vs CHICAGO CITY PUMAS 2019 | 66 | BYRD / ROOSEVELT PARK | |
| 6193 | Sat 10/25 9:30am | 10U/5CITY2 | CHICAGO CITY 2016 LOOP I vs NW 2016B PREMIER III | 16 | BRITISH SCHOOL TURF | |
| 6455* | Sat 10/25 10:00am |
15U-FS/2 | LIBERTYVILLE FC 1974-11A-FALL TEAM 1 vs CHICAGO CITY PUMAS 2011 | 1 | LTSC FLD | Field 14 |
| 6277 | Sat 10/25 10:30am | 12U/3CITY | CHICAGO CITY 2014 I vs IPROSKILLS 2014 SELECT ACADEMY | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 6321 | Sat 10/25 10:45am | 14U/3CITY | CHICAGO CITY 2012 II vs NW 2012B PREMIER I | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | |
| 6333 | Sat 10/25 11:00am | 11U/5CITY | CHICAGO KICS 2015 RED (CITY) vs CHICAGO CITY 2015 III | 25 | DUNBAR SOCCER COMPLEX | 9 v 9 |
| 6358* | Sat 10/25 11:00am | 11U/5S2 | KORA FC 2015 ELITE vs CHICAGO CITY 2015 SOUTH | 26 | CENTENNIAL PARK (ORLAND PARK) | Soccer 2 |
| 5213* | Sat 10/25 11:00am |
14U/5E2 | ELITE STRIKERS 2012/13 WHITE vs CHICAGO CITY 2012 III | 16 | FOX MEADOW | |
| 6098* | Sat 10/25 11:30am |
8U-7V7/4E | ELA ELITE 2018 vs CHICAGO CITY 2018 I | 1 | BUFFALO CREEK | 7v7 |
| 6487 | Sat 10/25 12:00pm | 8U-7V7/5E1 | PSG ACADEMY CHICAGO 2018 BLUE vs CHICAGO CITY 2018 II | 16 | CHICAGO HOPE ACADEMY TRACK & FIELD - USE FOR 5V5 & 7V7 GAMES | FIELD B 7V7 |
| 5504* | Sat 10/25 12:00pm |
10U/3S | CHICAGO CITY 2016 SOUTH I vs CHICAGO INTER ROGUE FC 2016 | 26 | EAGLE RIDGE II PARK | |
| 6541 | Sat 10/25 12:45pm | 9U/5CITY | CFYSC 2017B SELECT WHITE vs CHICAGO CITY 2017 I | 17 | FIRE PITCH | 7v7 Pitch 2-B |
| 6901* | Sat 10/25 1:30pm |
11U/4CITY | CHICAGO CITY 2015 II vs CFYSC 2015B SELECT | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 6122* | Sat 10/25 2:00pm |
11U/3CITY | IEFC WOLFPACK FC 2015 vs CHICAGO CITY 2015 ACADEMY II | 12 | HARRIET E SAYRE ELEMENTARY SCHOOL | |
| 6680 | Sat 10/25 2:00pm | 9U/4CITY | IPROSKILLS 2017 vs CHICAGO CITY 2017 ACADEMY II | 16 | ROGERS PARK | SMALL |
| 6725* | Sat 10/25 2:30pm | 13U/4CITY | ACADEMIA ATLAS 2013 BLACK vs CHICAGO CITY 2013 II | 32 | LAWLER PARK (CHICAGO) | |
| 4840* | Sat 10/25 2:45pm |
11U/4CITY | CFYSC 2015B SELECT RED vs CHICAGO CITY 2015 LOOP I | 17 | FIRE PITCH | 9v9 Pitch 1-1A |
| 4725* | Sat 10/25 3:00pm |
8U-7V7/5W | CHICAGO EMPIRE FC 2018 BLUE 2 vs CHICAGO CITY PUMAS 2018 | 17 | OAK BROOK POLO FIELDS | F 7v7 |
| 6764 | Sat 10/25 3:00pm | 12U/5CITY | CHICAGO CITY 2014 IV vs NORRIDGE UNITED 2014 SELECT | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 6800* | Sat 10/25 3:30pm |
10U/5CITY1 | PSG ACADEMY CHICAGO 2016 WHITE vs CHICAGO CITY 2016 II | 16 | JAMES OTIS SCHOOL FIELD - ONLY 7V7 GAMES | |
| 6425* | Sat 10/25 4:00pm | 9U/5W | CHICAGO CITY PUMAS 2017 BLUE vs AJAX FC NAPERVILLE 2017 BLACK | 10 | KEMPER PARK | |
| 6429* | Sat 10/25 4:00pm | 11U/2W | CHICAGO CITY PUMAS 2015 vs EGSC 2015 PREMIER | 10 | KEMPER PARK | |
| 6892 | Sat 10/25 4:15pm | 10U/5CITY1 | OPRF ALLIANCE 2016 vs CHICAGO CITY 2016 III | 12 | IRVING SCHOOL | |
| 5653* | Sat 10/25 4:30pm |
9U/5S | TESC 2017 PREMIER GREEN vs CHICAGO CITY 2017 SOUTH I | 17 | CONRAD FISCHER PARK | 7 vs 7 # 2 |
| 6873* | Sat 10/25 4:30pm |
10U/5S | LEGACY SC 2016 vs CHICAGO CITY 2016 SOUTH II | 26 | SPENCER SCHOOL CAMPUS | Field 12 - 7v7 |
| 6334* | Sat 10/25 5:00pm |
13U/5CITY | CHICAGO KICS 2013 RED (CITY) vs CHICAGO CITY 2013 III | 25 | ST IGNATIUS HS | Small |
| 6934 | Sat 10/25 5:00pm | 12U/2E | CHICAGO CITY 2014 ACADEMY II vs YSI FC 2014 | 16 | BRITISH SCHOOL TURF | |
| 1517* | Sat 10/25 5:45pm |
15U-FS/4E | CHICAGO CITY 2011 II vs CHICAGO EDGE B2011 8TH GRADE | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | 11v11 |
| 6335* | Sat 10/25 6:00pm |
14U/5E1 | CHICAGO KICS 2012 WHITE (CITY) vs CHICAGO CITY 2012 LOOP I | 25 | ST IGNATIUS HS | Small |
| 6955 | Sat 10/25 6:00pm | 12U/5CITY | NW 2014B PREMIER IV vs CHICAGO CITY 2014 III | 17 | UIC TURF FIELD EAST | |
| 6647* | Sat 10/25 11:30pm | 12U/4NW | ROCKFORD RAPTORS 2014 ORANGE vs CHICAGO CITY PUMAS 2014 | 9 | SPORTSCORE 2 & SPORTSCORE 1 (WTNG ON PD) | 216B |
| 6073 | Sun 10/26 9:00am | 10U/4W2 | RUSH WEST 2016 PREMIER 2 vs CHICAGO CITY PUMAS 2016 BLUE | 28 | HUMBRACHT FIELD | |
| 6462* | Sun 10/26 9:00am |
9U/5S | MUSTANGS UNITED FC 2017 vs CHICAGO CITY 2017 SOUTH I | 17 | MARTIN PARK | |
| 6223* | Sun 10/26 9:00am |
8U-7V7/5E2 | IPROSKILLS 2018 vs CHICAGO CITY 2018 III | 16 | ROGERS PARK | SMALL |
| 3893* | Sun 10/26 10:00am | 13U/4NW | CHICAGO CITY PUMAS SC 2013 BLUE vs SUFC 2013 ROCKFORD NEMEZIZ | 10 | KEMPER PARK | |
| 3490* | Sun 10/26 10:00am | 11U/1N | IPROSKILLS 2015 NEON vs CHICAGO CITY 2015 - CROATIA SC | 16 | ROGERS PARK | 2 |
| 5466* | Sun 10/26 10:30am |
10U/5S | UESC - CHICAGOLAND 2016 SEL OP vs CHICAGO CITY 2016 SOUTH II | 33 | COMMISSIONERS PARK (FRANKFORT) | 7v7 |
| 6427* | Sun 10/26 10:30am |
10U/3E | CHICAGO CITY 2016 ACADEMY II vs YSI FC 2016 | 16 | BERNARD ZELL ANSHE EMET DAY SCHOOL | |
| 2853* | Sun 10/26 10:30am |
12U/3CITY | CHICAGO CITY 2014 I vs CHICAGO KICS 2014 BLUE (CITY) | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 6322 | Sun 10/26 10:45am | 13U/3E | PEGASUS FC/1974 (2013) BLACK vs CHICAGO CITY 2013 I | 16 | WILLOW HILL PARK | #2 |
| 4650* | Sun 10/26 11:00am |
10U/3S | CHICAGO CITY 2016 SOUTH I vs CHICAGO DYNASTY FC 2016B RED | 26 | CENTENNIAL PARK (ORLAND PARK) | |
| 6206 | Sun 10/26 11:30am | 11U/4CITY | CHICAGO KICS 2015 BLUE (CITY) vs CHICAGO CITY 2015 I | 25 | DUNBAR GRASS | 9 v 9 |
| 6550* | Sun 10/26 11:30am |
12U/4CITY | CHICAGO KNIGHTS 14/15 vs CHICAGO CITY 2014 LOOP I | 17 | LAWLER PARK (CHICAGO) | |
| 4724* | Sun 10/26 12:00pm | 14U/5E2 | CHICAGO EDGE B2012 COMPETITIVE vs CHICAGO CITY 2012 III | 12 | KEYSTONE PARK | East |
| 6915* | Sun 10/26 12:00pm |
15U-FS/4E | NW 2011B PREMIER FS vs CHICAGO CITY 2011 II | 17 | FOSTER AVENUE FIELDS | 1 |
| 6533 | Sun 10/26 12:30pm | 10U/2N | PEGASUS FC/1974 (2016) RED vs CHICAGO CITY PUMAS 2016 GOLD | 16 | WOODLAND PARK (DEERFIELD) | Small |
| 6583* | Sun 10/26 1:00pm |
8U-7V7/5W | NAZ UNITED F.C. - 2018 ELITE vs CHICAGO CITY PUMAS 2018 | 17 | NAZARENE UNITED | |
| 6729* | Sun 10/26 1:00pm | 10U/5CITY1 | CHICAGO KNIGHTS 2016 vs CHICAGO CITY 2016 III | 17 | BRIGHTON PARK COMMUNITY CAMPUS | |
| 4861 | Sun 10/26 1:00pm | 11U/3CITY | CHICAGO KICS 2015 PRE-ACADEMY (CITY) vs CHICAGO CITY 2015 ACADEMY II | 25 | DUNBAR SOCCER COMPLEX | turf field |
| 6426* | Sun 10/26 1:30pm |
10U/2E | CHICAGO CITY 2016 ACADEMY I vs BERBER CITY FC 2016 | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 5588* | Sun 10/26 2:00pm | 9U/5W | CHICAGO CITY PUMAS 2017 BLUE vs KANELAND UNITED 2017 | 10 | KEMPER PARK | |
| 6527* | Sun 10/26 2:15pm |
11U/4CITY | CHICAGO CITY 2015 LOOP I vs CFYSC 2015B SELECT | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | |
| 6956* | Sun 10/26 2:30pm |
12U/4CITY | PSG ACADEMY CHICAGO 2014 BLUE vs CHICAGO CITY 2014 II | 16 | LIVINGSTON FIELD - USE FOR 9V9 GAMES ONLY - FALL 2025 | |
| 4925* | Sun 10/26 3:00pm |
12U/5CITY | CHICAGO CITY 2014 III vs BERBER CITY FC 2014 | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 5458* | Sun 10/26 4:00pm |
8U-7V7/4E | PRSC 2018 ORANGE vs CHICAGO CITY 2018 I | 4 | EMERSON MIDDLE SCHOOL | NW |
| 3890* | Sun 10/26 4:00pm | 9U/3NW | CHICAGO CITY PUMAS 2017 vs PALATINE CELTIC 2017 BLACK | 10 | KEMPER PARK | |
| 6663* | Sun 10/26 4:00pm |
10U/5CITY2 | CHICAGO KICS 2016 BLUE (NORTH) vs CHICAGO CITY 2016 IV | 25 | DUNBAR GRASS | |
| 1673* | Sun 10/26 4:00pm |
11U/5S2 | LEGACY SC 2015 SELECT vs CHICAGO CITY 2015 SOUTH | 26 | SPENCER SCHOOL CAMPUS | Field 7 - 9v9 |
| 2917* | Sun 10/26 4:30pm |
9U/3E | CHICAGO CITY 2017 ACADEMY I vs CHICAGO CELTIC SC 2017 GREEN | 16 | LYCEE DE FRANCAIS SCHOOL | |
| 6914 | Sun 10/26 4:30pm | 14U/5E1 | NW 2012B PREMIER II vs CHICAGO CITY 2012 IV | 17 | FOSTER AVENUE FIELDS | I |
| 2761* | Sun 10/26 5:45pm |
13U/4CITY | CHICAGO CITY 2013 LOOP I vs NW 2013B PREMIER II | 16 | WELLS COMMUNITY ACADEMY HIGH SCHOOL | |
| 5923* | Sun 10/26 7:00pm* Submitted |
10U/4CITY | PSG ACADEMY CHICAGO 2016 BLUE vs CHICAGO CITY 2016 I | 16 | UIC TURF FIELD EAST | |
| 4748* | Mon 10/27 8:00pm |
12U/4S | CHICAGO CITY 2014 SOUTH vs ORLAND PARK STING FC 2014 ELITE | 26 | CENTENNIAL PARK (ORLAND PARK) | Field # 3 |
| 5293* | Tue 10/28 8:30pm |
15U-FS/2 | GALAXY 2011 SELECT FALL TRAPPED vs CHICAGO CITY PUMAS 2011 | 6 | KNOCH PARK |