| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 3691* | Thu 10/22 6:00pm |
U10/5E1 | CFA - JAHBAT B2016/17 YELLOW vs OLYMPIACOS 16/17 PREMIER | 16 | ROBERT CROWN COMMUNITY CENTER | FIELD 1 |
| 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 |
| 1025* | Sat 10/24 11:15am |
U09/4E | FCS EVANSTON 17/18 BOYS ORANGE vs OLYMPIACOS 17/18 ELITE | 3 | JAMES PARK | 1B |
| 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 |
| 2326* | Sat 10/24 3:00pm | U12/2E | IPROSKILLS 2014/15 NEON vs OLYMPIACOS 14/15 ELITE | 16 | ROGERS PARK | #3 |
| 5679* | Sat 10/24 6:00pm |
U11/2E | CFA - JAHBAT B2015/16 GREEN vs OLYMPIACOS 15/16 ELITE | 16 | ROBERT CROWN COMMUNITY CENTER | Field 2 |
| 1960* | Sun 10/25 8:30am |
U12/2E | CFA - JAHBAT B2014/15 PREMIER vs OLYMPIACOS 14/15 ELITE | 16 | ROBERT CROWN COMMUNITY CENTER | Field 1 |
| 3148* | Sun 10/25 9:00am |
U08-5V5/4N | OLYMPIACOS 18/19 ELITE vs FORCE 18/19B ELITE | 3 | HELLENIC AMERICAN ACADEMY | |
| 4139* | Sun 10/25 10:15am |
U10/5E1 | TREVIAN 16/17 WHITE COPA vs OLYMPIACOS 16/17 PREMIER | 16 | AVOCA FIELD | B1 |
| 4737* | Sun 10/25 11:30am | U09/4E | OLYMPIACOS 17/18 ELITE vs CHICAGO CELTIC SC 17/18 GREEN | 3 | HELLENIC AMERICAN ACADEMY | 7v7 |
| 5101* | Sun 10/25 3:00pm | U12/4E2 | CHICAGO PHOENIX FC 14/15 vs OLYMPIACOS 14/15 PREMIER | 32 | TERRACE SCHOOL |