| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 63 | Sat 9/12 9:00am | U07-4V4/N | OLYMPIACOS 19/20 ELITE vs REAL MADRID ROUND LAKE F.C 19/20 ELITE | 66 | HELLENIC AMERICAN ACADEMY | 4v4 |
| 108 | Sat 9/12 9:00am | U08-5V5/4N | FORCE 18/19B ELITE vs OLYMPIACOS 18/19 ELITE | 14 | LIPPOLD PARK SOCCER COMPLEX | FIELD 18 |
| 177 | Sat 9/12 10:00am | U10/5E1 | OLYMPIACOS 16/17 PREMIER vs NORRIDGE UNITED 16/17 SELECT | 4 | HELLENIC AMERICAN ACADEMY | 7v7 |
| 351* | Sat 9/12 10:30am |
U10/1 | ORLAND PARK STING FC 16/17 PREMIER vs OLYMPIACOS 16/17 ELITE | 26 | CENTENNIAL PARK (ORLAND PARK) | Field 7 |
| 297 | Sat 9/12 11:30am | U09/4E | CFYSC 18/19 SELECT U8 vs OLYMPIACOS 17/18 ELITE | 17 | FIRE PITCH | 7v7 Pitch 2-A |
| 429 | Sat 9/12 1:00pm | U11/2E | OLYMPIACOS 15/16 ELITE vs YSI FC 15/16 TEAM | 4 | TO BE DETERMINED | #2 |
| 525 | Sat 9/12 2:00pm | U12/2E | OLYMPIACOS 14/15 ELITE vs RUSH - WILMETTE WINGS 14/15B PREMIER | 4 | TO BE DETERMINED | #2 |
| 537 | Sat 9/12 2:00pm | U12/4E2 | ELITE STRIKERS 14/15 vs OLYMPIACOS 14/15 PREMIER | 16 | FOX MEADOW | |
| 660 | Sat 9/12 4:00pm | U13/3N | OLYMPIACOS 13/14 ELITE vs NSFC 13/14 ELITE | 4 | TO BE DETERMINED | #2 |
| 1372* | Sun 9/13 4:30pm |
U12/4E2 | RUSH - WILMETTE WINGS 14/15B BLUE vs OLYMPIACOS 14/15 PREMIER | 16 | WILMETTE COMMUNITY PLAYFIELD | 3 |
| 748 | Sat 9/19 8:00am | U11/2E | NORRIDGE UNITED 15/16 PREMIER vs OLYMPIACOS 15/16 ELITE | 4 | NORRIDGE PARK | |
| 785 | Sat 9/19 9:00am | U07-4V4/N | OLYMPIACOS 19/20 ELITE vs HOTC 19/20 | 66 | HELLENIC AMERICAN ACADEMY | 4v4 |
| 934 | Sat 9/19 10:00am | U10/5E1 | OLYMPIACOS 16/17 PREMIER vs FC STARS 16/17 SELECT | 4 | HELLENIC AMERICAN ACADEMY | 7v7 |
| 1025* | Sat 9/19 10:15am |
U09/4E | FCS EVANSTON 17/18 BOYS ORANGE vs OLYMPIACOS 17/18 ELITE | 3 | JAMES PARK | 1B |
| 1283 | Sat 9/19 2:00pm | U12/2E | OLYMPIACOS 14/15 ELITE vs CFA - JAHBAT B2014/15 PREMIER | 4 | TO BE DETERMINED | #2 |
| 1426 | Sat 9/19 4:00pm | U13/3N | OLYMPIACOS 13/14 ELITE vs NORRIDGE UNITED 13/14 PREMIER | 4 | TO BE DETERMINED | #2 |
| 1433 | Sat 9/19 4:00pm | U10/1 | AAC EAGLES CHICAGO 16/17 GOLD vs OLYMPIACOS 16/17 ELITE | 7 | UDALL PARK | 7V7 |
| 3231* | Sun 9/20 10:30am |
U10/1 | WCOB FC 2016/17 SELECT vs OLYMPIACOS 16/17 ELITE | 17 | CENTRAL PARK NORTH - KENSINGTON RD. ENTRANCE | 8 |
| 1543 | Sat 9/26 9:00am | U07-4V4/N | HOTC 19/20 vs OLYMPIACOS 19/20 ELITE | 66 | WAUKEGAN SPORTS PARK | 7v7 |
| 1617 | Sat 9/26 10:00am | U08-5V5/4N | OLYMPIACOS 18/19 ELITE vs CHICAGO CITY 18/19 I | 4 | TO BE DETERMINED | #2 |
| 1711 | Sat 9/26 10:45am | U13/3N | HAWTHORN WOODS ELITE 13/14 vs OLYMPIACOS 13/14 ELITE | 7 | HERITAGE OAKS | BIG FIELD |
| 1735 | Sat 9/26 11:00am | U09/4E | OLYMPIACOS 17/18 ELITE vs CFYSC 17/18 SELECT U9 | 4 | TO BE DETERMINED | #2 |
| 1859 | Sat 9/26 12:00pm | U10/5E1 | ELITE STRIKERS FC 16/17 vs OLYMPIACOS 16/17 PREMIER | 16 | FOX MEADOW | |
| 1864 | Sat 9/26 12:00pm | U12/4E2 | CHICAGO CELTIC SC 14/15 WHITE II vs OLYMPIACOS 14/15 PREMIER | 4 | EDISON PARK ELEMENTARY | |
| 1960 | Sat 9/26 1:30pm | U12/2E | CFA - JAHBAT B2014/15 PREMIER vs OLYMPIACOS 14/15 ELITE | 16 | ROBERT CROWN COMMUNITY CENTER | Field 2 |
| 2058 | Sat 9/26 2:30pm | U10/1 | ACADEMIA ATLAS FC 16/17 SELECT vs OLYMPIACOS 16/17 ELITE | 32 | VITTUM PARK | 7V7 |
| 2025 | Sun 9/27 2:00pm | U11/2E | BVB IA CHICAGO 15/16 YELLOW vs OLYMPIACOS 15/16 ELITE | 7 | BURNING BUSH TRAILS PARK | |
| 2312 | Sat 10/3 9:00am | U08-5V5/4N | PRSC 19/20 ORANGE vs OLYMPIACOS 18/19 ELITE | 4 | EMERSON MIDDLE SCHOOL | NW |
| 2326 | Sat 10/3 9:00am | U12/2E | IPROSKILLS 2014/15 NEON vs OLYMPIACOS 14/15 ELITE | 16 | ROGERS PARK | #3 |
| 2439 | Sat 10/3 10:00am | U10/5E1 | OLYMPIACOS 16/17 PREMIER vs CHICAGO PHOENIX FC 16/17 BLACK | 4 | HELLENIC AMERICAN ACADEMY | 7v7 |
| 2708 | Sat 10/3 1:00pm | U11/2E | OLYMPIACOS 15/16 ELITE vs IPROSKILLS 2015/16 NEON | 4 | TO BE DETERMINED | #2 |
| 2876 | Sat 10/3 3:00pm | U12/4E2 | OLYMPIACOS 14/15 PREMIER vs CHICAGO FC UNITED 14/15 PRE-ACADEMY II | 4 | TO BE DETERMINED | #2 |
| 2942 | Sat 10/3 4:00pm | U07-4V4/N | NSFC 19/20 SPURS vs OLYMPIACOS 19/20 ELITE | 66 | LAKE FOREST HIGH SCHOOL WEST CAMPUS | Field 6 (4v4) |
| 2944 | Sat 10/3 4:00pm | U13/3N | OLYMPIACOS 13/14 ELITE vs FC-1 13/14 PRE-ACADEMY | 4 | TO BE DETERMINED | #2 |
| 3148 | Sat 10/10 10:00am | U08-5V5/4N | OLYMPIACOS 18/19 ELITE vs FORCE 18/19B ELITE | 4 | TO BE DETERMINED | #2 |
| 3267 | Sat 10/10 11:00am | U09/4E | OLYMPIACOS 17/18 ELITE vs IPROSKILLS ACADEMY 2017/18 | 4 | TO BE DETERMINED | #2 |
| 3384 | Sat 10/10 12:00pm | U07-4V4/N | LBR MUNDELEIN LIONS B19/20 vs OLYMPIACOS 19/20 ELITE | 66 | FREMONT SCHOOL (NO PETS) | 5v5 |
| 3464 | Sat 10/10 1:15pm | U12/2E | CFYSC 14/15 PREMIER WHITE U12 vs OLYMPIACOS 14/15 ELITE | 17 | FIRE PITCH | 9v9 Pitch 1-B |
| 3571 | Sat 10/10 2:45pm | U12/4E2 | CHICAGO MAGIC 14/15 ELITE vs OLYMPIACOS 14/15 PREMIER | 16 | LINCOLN SCHOOL SOCCER FIELD | |
| 3691 | Sun 10/11 4:30pm | U10/5E1 | CFA - JAHBAT B2016/17 YELLOW vs OLYMPIACOS 16/17 PREMIER | 16 | EVANSTON TOWNSHIP HIGH SCHOOL | 7v7 Grass Field |
| 3914 | Sat 10/17 10:15am | U08-5V5/4N | CFYSC 18/19 SELECT WHITE U8 vs OLYMPIACOS 18/19 ELITE | 17 | FIRE PITCH | PITCH 2 / 2-A 5V5 |
| 3981 | Sat 10/17 11:00am | U09/4E | OLYMPIACOS 17/18 ELITE vs BVB IA CHICAGO 17/18 YELLOW | 4 | TO BE DETERMINED | #2 |
| 4116 | Sat 10/17 12:00pm | U13/3N | SCOUTS FC 2013/14 vs OLYMPIACOS 13/14 ELITE | 16 | ROUND LAKE AREA PARK DISTRICT (SPORTS CENTER) - DO NOT USE | |
| 4088* | Sat 10/17 12:15pm | U10/1 | LASC 16/17 ELITE PRE N1 vs OLYMPIACOS 16/17 ELITE | 16 | LAKE VILLA TOWNSHIP SOCCER COMPLEX | |
| 4127 | Sat 10/17 12:30pm | U12/2E | RUSH - WILMETTE WINGS 14/15B PREMIER vs OLYMPIACOS 14/15 ELITE | 16 | WEST PARK | Medium (9v9) |
| 4139 | Sat 10/17 12:45pm | U10/5E1 | TREVIAN 16/17 WHITE COPA vs OLYMPIACOS 16/17 PREMIER | 16 | FOX MEADOW | 7v7- East Field |
| 4169 | Sat 10/17 1:00pm | U11/2E | OLYMPIACOS 15/16 ELITE vs RUSH - WILMETTE WINGS 15/16B PREMIER TIEMPO | 4 | TO BE DETERMINED | #2 |
| 4335 | Sat 10/17 3:00pm | U12/4E2 | OLYMPIACOS 14/15 PREMIER vs ELITE STRIKERS 14/15 | 4 | TO BE DETERMINED | #2 |
| 3758 | Sun 10/18 9:00am | U07-4V4/N | REAL MADRID ROUND LAKE F.C 19/20 ELITE vs OLYMPIACOS 19/20 ELITE | 66 | LAKEWOOD GROVE PARK | |
| 2650* | Sun 10/18 12:00pm |
U09/4E | NORTHWIND SC 17/18 PREMIER 1 vs OLYMPIACOS 17/18 ELITE | 17 | FOSTER AVENUE FIELDS | II |
| 2618* | Sat 10/24 9:00am |
U10/1 | EVOLUTION SC 16/17 PRE ACADEMY BOYS PFC vs OLYMPIACOS 16/17 ELITE | 6 | WEST HILLS COMMUNITY CHURCH | 1 |
| 4530 | Sat 10/24 9:00am | U07-4V4/N | OLYMPIACOS 19/20 ELITE vs NSFC 19/20 FIRE | 66 | HELLENIC AMERICAN ACADEMY | 4v4 |
| 4547 | Sat 10/24 9:00am | U11/2E | PRSC 15/16 ORANGE vs OLYMPIACOS 15/16 ELITE | 4 | WOODLAND PARK | SE |
| 4662 | Sat 10/24 10:15am | U10/5E1 | FC MIRAGE 2016/17 BLACK vs OLYMPIACOS 16/17 PREMIER | 3 | WILLOW HILL PARK | 7v7 A |
| 4737 | Sat 10/24 11:00am | U09/4E | OLYMPIACOS 17/18 ELITE vs CHICAGO CELTIC SC 17/18 GREEN | 4 | TO BE DETERMINED | #2 |
| 4745 | Sat 10/24 11:00am | U10/1 | PRSC 16/17 ORANGE vs OLYMPIACOS 16/17 ELITE | 4 | EMERSON MIDDLE SCHOOL | NC |
| 4647* | Sat 10/24 1:00pm |
U13/3N | LBR MUNDELEIN LIONS B13/14 vs OLYMPIACOS 13/14 ELITE | 35 | FREMONT SCHOOL (NO PETS) | Field 4 |
| 4988 | Sat 10/24 2:00pm | U12/2E | OLYMPIACOS 14/15 ELITE vs CHICAGO FC UNITED 14/15 PRE-ACADEMY I TEAM II | 4 | TO BE DETERMINED | #2 |
| 5101 | Sat 10/24 3:00pm | U12/4E2 | CHICAGO PHOENIX FC 14/15 vs OLYMPIACOS 14/15 PREMIER | 32 | PRAIRIE LAKES PK FLDS | |
| 5254 | Sat 10/31 9:00am | U07-4V4/N | OLYMPIACOS 19/20 ELITE vs LBR MUNDELEIN LIONS B19/20 | 66 | HELLENIC AMERICAN ACADEMY | 4v4 |
| 5365 | Sat 10/31 10:00am | U08-5V5/4N | OLYMPIACOS 18/19 ELITE vs CFYSC 18/19 SELECT WHITE U8 | 4 | TO BE DETERMINED | #2 |
| 5411 | Sat 10/31 10:00am | U10/5E1 | OLYMPIACOS 16/17 PREMIER vs ELITE STRIKERS FC 16/17 | 4 | HELLENIC AMERICAN ACADEMY | 7v7 |
| 5587 | Sat 10/31 12:00pm | U10/1 | OLYMPIACOS 16/17 ELITE vs CFYSC 16/17 PREMIER RED U10 | 4 | TO BE DETERMINED | #2 |
| 5679 | Sat 10/31 1:00pm | U11/2E | OLYMPIACOS 15/16 ELITE vs CFA - JAHBAT B2015/16 GREEN | 4 | TO BE DETERMINED | #2 |
| 5762 | Sat 10/31 2:00pm | U12/2E | OLYMPIACOS 14/15 ELITE vs CFYSC 14/15 PREMIER WHITE U12 | 4 | TO BE DETERMINED | #2 |
| 5853 | Sat 10/31 3:00pm | U12/4E2 | OLYMPIACOS 14/15 PREMIER vs CHICAGO CELTIC SC 14/15 WHITE II | 4 | TO BE DETERMINED | #2 |
| 5908 | Sat 10/31 4:00pm | U13/3N | OLYMPIACOS 13/14 ELITE vs HAWTHORN WOODS ELITE 13/14 | 4 | TO BE DETERMINED | #2 |
| 5957 | Sat 10/31 5:30pm | U09/4E | RUSH - WILMETTE WINGS 17/18B PREMIER vs OLYMPIACOS 17/18 ELITE | 16 | WILMETTE COMMUNITY PLAYFIELD | Field #4 7v7 |
| 2266 | Thu 12/31 9:00am | U08-5V5/4N | CHICAGO CITY 18/19 I vs OLYMPIACOS 18/19 ELITE | 16 | BELDING SCHOOL | 5v5 |
| 887 | Thu 12/31 10:00am | U08-5V5/4N | OLYMPIACOS 18/19 ELITE vs PRSC 19/20 ORANGE | 4 | TO BE DETERMINED | #2 |
| 1650 | Thu 12/31 10:15am | U11/2E | CFYSC 16/17 PREMIER U10 vs OLYMPIACOS 15/16 ELITE | 17 | FIRE PITCH | 9v9 Pitch 1-A |
| 3523 | Thu 12/31 12:00pm | U13/3N | FC 1974 LIBERTYVILLE SELECT 2 B2013/14 vs OLYMPIACOS 13/14 ELITE | 16 | LTSC FLD | Field 14 |