| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 7 | Sat 9/6 8:00am | 8U-5V5/4N | NORRIDGE UNITED 2018 PREMIER vs OLYMPIACOS 2018 | 4 | DIVINE SAVIOR CHURCH | |
| 81 | Sat 9/6 9:00am | 12U/4E | IPROSKILLS 2014 BLACK vs OLYMPIACOS 2014/2015 PREMIER | 16 | ROGERS PARK | #3 |
| 106 | Sat 9/6 9:00am | 9U/1 | OLYMPIACOS 2017 ELITE vs GLEN ELLYN LAKERS 2017 ELITE | 4 | MAIN EAST HIGH SCHOOL | |
| 305 | Sat 9/6 11:00am | 9U/3E | OLYMPIACOS 2017 PREMIER vs SAA UNITED SC 2017 BLACK | 4 | MAIN EAST HIGH SCHOOL | |
| 306 | Sat 9/6 11:00am | 11U/3E | OLYMPIACOS 2015 ELITE vs CHICAGO MAGIC 2015 | 4 | MAIN EAST HIGH SCHOOL | |
| 418 | Sat 9/6 12:00pm | 10U/3NW | OLYMPIACOS 2016 PREMIER vs ELA ELITE 2016 PREMIER | 4 | MAIN EAST HIGH SCHOOL | |
| 182* | Sat 9/6 1:30pm |
10U/2N | OLYMPIACOS 2016 ELITE vs PEGASUS FC/1974 (2016) RED | 4 | MAIN EAST HIGH SCHOOL | |
| 260 | Sun 9/7 10:45am | 13U/3E | PEGASUS FC/1974 (2013) BLACK vs OLYMPIACOS 2013/2014 ELITE | 16 | WILLOW HILL PARK | #2 |
| 3402* | Sun 9/7 11:00am |
10U/3NW | LIBERTYVILLE FC 1974-16A-ORANGE 1 vs OLYMPIACOS 2016 PREMIER | 1 | LTSC FLD | Field 17c |
| 4563* | Sun 9/7 2:00pm |
8U-5V5/4N | OLYMPIACOS 2018 vs CFYSC 2018B SELECT RED | 4 | MAIN EAST HIGH SCHOOL | |
| 2813* | Sun 9/7 2:00pm |
10U/2N | OLYMPIACOS 2016 ELITE vs CHICAGO CITY PUMAS 2016 GOLD | 4 | MAIN EAST HIGH SCHOOL | |
| 4671* | Thu 9/11 5:30pm |
11U/3E | OLYMPIACOS 2015 ELITE vs LEO SOCCER SCHOOL 2015 | 4 | MAIN EAST HIGH SCHOOL | |
| 2221* | Thu 9/11 5:30pm |
12U/4E | OLYMPIACOS 2014/2015 PREMIER vs HUSSARS UNITED 2014 | 4 | MAIN EAST HIGH SCHOOL | |
| 1032 | Sat 9/13 9:30am | 10U/2N | FORCE 2016B ELITE POOL II vs OLYMPIACOS 2016 ELITE | 1 | LIPPOLD PARK SOCCER COMPLEX | FIELD 7 |
| 1034 | Sat 9/13 9:30am | 12U/4E | IP-SKOMOR 2014 PREMIER II vs OLYMPIACOS 2014/2015 PREMIER | 16 | HAMLIN PARK | |
| 1212 | Sat 9/13 11:00am | 9U/3E | OLYMPIACOS 2017 PREMIER vs CHICAGO CELTIC SC 2017 GREEN | 4 | MAIN EAST HIGH SCHOOL | |
| 1406 | Sat 9/13 1:00pm | 13U/3E | OLYMPIACOS 2013/2014 ELITE vs CFA-JAHBAT FC B2013 GREEN | 4 | MAIN EAST HIGH SCHOOL | |
| 990* | Sat 9/13 2:00pm |
9U/1 | OLYMPIACOS 2017 ELITE vs AAC EAGLES CHICAGO 2017 RED | 4 | MAIN EAST HIGH SCHOOL | |
| 1285 | Sun 9/14 12:00pm | 11U/3E | FC-1 ACADEMY 2015 SELECT BLUE 1 vs OLYMPIACOS 2015 ELITE | 16 | COMMUNITY PARK WEST (GLENVIEW) | 3 - (9 v 9) |
| 1316* | Sun 9/14 12:30pm |
10U/3NW | OLYMPIACOS 2016 PREMIER vs 60 UNITED - LFSA 2016 BLUE | 4 | MAIN EAST HIGH SCHOOL | |
| 1429 | Sun 9/14 1:00pm | 8U-5V5/4N | WEST CHICAGO FC 2018 RED vs OLYMPIACOS 2018 | 28 | CORNERSTONE LAKES PARK | |
| 1819 | Sat 9/20 9:00am | 8U-5V5/4N | FCS TEAM EVANSTON 2018 BOYS ORANGE I vs OLYMPIACOS 2018 | 16 | JAMES PARK | #1 |
| 1931 | Sat 9/20 10:00am | 10U/2N | OLYMPIACOS 2016 ELITE vs ELA ELITE 2016 | 4 | MAIN EAST HIGH SCHOOL | |
| 2016 | Sat 9/20 10:45am | 10U/3NW | 60 UNITED - LFSA 2016 BLUE vs OLYMPIACOS 2016 PREMIER | 1 | DEERPATH COMMUNITY PARK (LAKE FOREST) | 7v7 |
| 2068 | Sat 9/20 11:00am | 11U/3E | UESC - LAKE FC 2015 vs OLYMPIACOS 2015 ELITE | 16 | ZION PARK DISTRICT | 9v9 |
| 2207 | Sat 9/20 12:00pm | 9U/1 | WCOB FC 2017 SELECT vs OLYMPIACOS 2017 ELITE | 17 | CENTRAL PARK NORTH (OAK BROOK) | Field 8 |
| 2307 | Sat 9/20 1:30pm | 9U/3E | CHICAGO CELTIC SC 2017 GREEN vs OLYMPIACOS 2017 PREMIER | 4 | HITCH ELEMENTARY SCHOOL | |
| 2373 | Sat 9/20 2:00pm | 13U/3E | PRSC 2013 BLACK vs OLYMPIACOS 2013/2014 ELITE | 4 | WOODLAND PARK | SW |
| 2624 | Sat 9/27 8:00am | 8U-5V5/4N | OLYMPIACOS 2018 vs WCOB FC 2018 SELECT | 4 | MAIN EAST HIGH SCHOOL | |
| 2726* | Sat 9/27 12:00pm |
9U/1 | OLYMPIACOS 2017 ELITE vs ECS 2017 B ELITE | 4 | MAIN EAST HIGH SCHOOL | |
| 2789* | Sat 9/27 12:00pm |
9U/3E | FC STARS 2017B BLACK vs OLYMPIACOS 2017 PREMIER | 16 | NILES WEST HIGH SCHOOL | Grass Fields 1 |
| 3191 | Sat 9/27 1:30pm | 12U/4E | FC-1 ACADEMY 2014 SELECT BLUE vs OLYMPIACOS 2014/2015 PREMIER | 16 | COMMUNITY PARK WEST (GLENVIEW) | 3 - (9 v 9) |
| 3478 | Sat 9/27 4:45pm | 13U/3E | IP-SKOMOR 2013 PREMIER vs OLYMPIACOS 2013/2014 ELITE | 16 | GOLF MIDDLE SCHOOL | |
| 2942* | Sun 9/28 9:00am |
11U/3E | OLYMPIACOS 2015 ELITE vs FCS LAKESHORE 2015 BOYS PREMIER | 4 | MAIN EAST HIGH SCHOOL | |
| 3527 | Sat 10/4 8:00am | 8U-5V5/4N | OLYMPIACOS 2018 vs NORRIDGE UNITED 2018 PREMIER | 4 | MAIN EAST HIGH SCHOOL | |
| 3976 | Sat 10/4 12:30pm | 12U/4E | OLYMPIACOS 2014/2015 PREMIER vs CHICAGO CELTIC SC 2014 WHITE | 4 | MAIN EAST HIGH SCHOOL | |
| 3587* | Sat 10/4 1:00pm |
10U/3NW | FC LAKE COUNTY 2016 SELECT 1 vs OLYMPIACOS 2016 PREMIER | 1 | ALLEGHANY PARK | AH 2 |
| 4029 | Sat 10/4 1:00pm | 13U/3E | OLYMPIACOS 2013/2014 ELITE vs FC STARS 2013B PREMIER | 4 | MAIN EAST HIGH SCHOOL | |
| 3839* | Sat 10/4 4:15pm |
9U/1 | CFYSC 2017B PREMIER RED vs OLYMPIACOS 2017 ELITE | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 3674* | Sat 10/4 7:00pm |
9U/3E | BARCA ACADEMY CHICAGO 2017 BLAU vs OLYMPIACOS 2017 PREMIER | 7 | OLYMPIC PARK FIELD | Field 7 |
| 4830* | Sun 10/5 12:00pm |
12U/4E | OLYMPIACOS 2014/2015 PREMIER vs CFYSC 2014B SELECT RED | 4 | MAIN EAST HIGH SCHOOL | |
| 3972 | Sun 10/5 12:30pm | 10U/2N | PEGASUS FC/1974 (2016) RED vs OLYMPIACOS 2016 ELITE | 16 | WOODLAND PARK (DEERFIELD) | Small |
| 4460 | Sat 10/11 9:00am | 9U/3E | SAA UNITED SC 2017 BLACK vs OLYMPIACOS 2017 PREMIER | 7 | OLYMPIC PARK FIELD | 5b (one half of fiel |
| 4540 | Sat 10/11 10:00am | 10U/2N | OLYMPIACOS 2016 ELITE vs FORCE 2016B ELITE POOL II | 4 | MAIN EAST HIGH SCHOOL | |
| 4872 | Sat 10/11 1:00pm | 10U/3NW | ELA ELITE 2016 PREMIER vs OLYMPIACOS 2016 PREMIER | 1 | BUFFALO CREEK | 7v7 |
| 4926 | Sun 10/12 1:30pm | 9U/1 | DEPORTIVO 2017 TURICATO FC vs OLYMPIACOS 2017 ELITE | 32 | MINUTEMAN PARK | |
| 1995* | Sun 10/12 2:15pm |
11U/3E | FC MIRAGE 2015 RED vs OLYMPIACOS 2015 ELITE | 16 | WILLOW HILL PARK | 9v9B |
| 5231 | Sat 10/18 8:00am | 8U-5V5/4N | OLYMPIACOS 2018 vs WEST CHICAGO FC 2018 RED | 4 | MAIN EAST HIGH SCHOOL | |
| 5256 | Sat 10/18 9:00am | 9U/1 | FORCE 2017B ELITE BLUE vs OLYMPIACOS 2017 ELITE | 1 | LIPPOLD PARK SOCCER COMPLEX | FIELD 6 |
| 5461* | Sat 10/18 10:00am | 10U/2N | ROCKFORD RAPTORS 2016 vs OLYMPIACOS 2016 ELITE | 9 | SPORTSCORE 2 & SPORTSCORE 1 (WTNG ON PD) | |
| 5534 | Sat 10/18 11:00am | 9U/3E | OLYMPIACOS 2017 PREMIER vs CHICAGO CITY 2017 ACADEMY I | 4 | MAIN EAST HIGH SCHOOL | |
| 5634 | Sat 10/18 12:00pm | 10U/3NW | OLYMPIACOS 2016 PREMIER vs LASC 2016 PREMIER | 4 | MAIN EAST HIGH SCHOOL | |
| 5640 | Sat 10/18 12:00pm | 11U/3E | PRSC 2015 ORANGE II vs OLYMPIACOS 2015 ELITE | 4 | WOODLAND PARK | SE |
| 5682 | Sat 10/18 12:30pm | 12U/4E | OLYMPIACOS 2014/2015 PREMIER vs CFA-JAHBAT FC B2014 YELLOW | 4 | MAIN EAST HIGH SCHOOL | |
| 5724* | Sat 10/18 3:00pm |
13U/3E | OLYMPIACOS 2013/2014 ELITE vs CHICAGO CITY 2013 I | 4 | MAIN EAST HIGH SCHOOL | |
| 6373* | Sun 10/19 12:00pm |
11U/3E | OLYMPIACOS 2015 ELITE vs CHICAGO FC UNITED 2015 PRE-ACADEMY I | 4 | MAIN EAST HIGH SCHOOL | |
| 6151 | Sat 10/25 9:00am | 9U/1 | OLYMPIACOS 2017 ELITE vs FC-1 ACADEMY 2017 ELITE | 4 | MAIN EAST HIGH SCHOOL | |
| 6476* | Sat 10/25 10:00am |
10U/3NW | OLYMPIACOS 2016 PREMIER vs FC LAKE COUNTY 2016 SELECT 1 | 4 | MAIN EAST HIGH SCHOOL | |
| 6372 | Sat 10/25 11:00am | 9U/3E | OLYMPIACOS 2017 PREMIER vs BARCA ACADEMY CHICAGO 2017 BLAU | 4 | MAIN EAST HIGH SCHOOL | |
| 6584 | Sat 10/25 1:00pm | 13U/3E | OLYMPIACOS 2013/2014 ELITE vs PRSC 2013 BLACK | 4 | MAIN EAST HIGH SCHOOL | |
| 6767 | Sat 10/25 3:00pm | 10U/2N | ELA ELITE 2016 vs OLYMPIACOS 2016 ELITE | 1 | BUFFALO CREEK | 7v7 |
| 6059* | Sun 10/26 10:00am |
8U-5V5/4N | OLYMPIACOS 2018 vs CFYSC 2018B SELECT RED | 4 | MAIN EAST HIGH SCHOOL | |
| 5186* | Sat 11/1 3:00pm |
13U/3E | CFYSC 2013B SELECT vs OLYMPIACOS 2013/2014 ELITE | 17 | MONTROSE FIELD | |
| 6953* | Sun 11/2 9:30am |
12U/4E | RUSH - WILMETTE WINGS 2014 WHITE vs OLYMPIACOS 2014/2015 PREMIER | 16 | WILMETTE COMMUNITY PLAYFIELD | Field #2 9v9 |