| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 5 | Sun 9/13 8:00am | U13/4S | AYSO 300 UNITED 13/14 B WHITE vs BLACK LIONS 13/14 | 17 | SEDGEWICK PARK | |
| 386* | Sun 9/13 12:00pm | U08-5V5/5SC1 | BLACK LIONS 18/19 vs BERBER CITY FC 18/19 | 17 | NEWCASTLE PARK | |
| 795* | Sun 9/20 1:00pm |
U08-5V5/5SC1 | CHICAGO KICS FC 18/19 BLUE SOUTH vs BLACK LIONS 18/19 | 25 | EVERGREEN PARK HIGH SCHOOL | 5v5 |
| 4120* | Sun 9/27 2:00pm | U08-5V5/5SC1 | BLACK LIONS 18/19 vs CHICAGO KICS FC 18/19 BLACK CITY | 17 | NEWCASTLE PARK | |
| 1640* | Sun 9/27 4:00pm | U13/4S | BLACK LIONS 13/14 vs CHICAGO EMPIRE FC 13/14 GOLD 2 | 17 | RICE PARK | |
| 3173* | Sat 10/3 9:00am | U13/4S | BLACK LIONS 13/14 vs LG CELTICS 2013/2014B GREEN | 17 | RICE PARK | |
| 2589* | Sat 10/3 12:00pm | U08-5V5/5SC1 | CHICAGO CITY 18/19 SOUTH I vs BLACK LIONS 18/19 | 26 | SUMMIT PARK (SUMMIT) | |
| 2689* | Sun 10/4 5:00pm |
U13/4S | UESC - CHICAGOLAND 13/14B SELECT BB vs BLACK LIONS 13/14 | 35 | DYNAMO FIELD | 11v11 |
| 3386* | Sun 10/11 12:00pm | U08-5V5/5SC1 | BLACK LIONS 18/19 vs LG CELTICS 2018/2019 BLACK | 17 | NEWCASTLE PARK | |
| 3902* | Sat 10/17 10:00am | U13/4S | BLACK LIONS 13/14 vs AYSO 300 UNITED 13/14 B WHITE | 17 | RICE PARK | |
| 1875* | Sat 10/17 1:00pm | U08-5V5/5SC1 | BLACK LIONS 18/19 vs LTSC 2018/19 TRAVEL WHITE | 17 | NEWCASTLE PARK | |
| 931* | Sun 10/18 3:30pm |
U13/4S | BLACK LIONS 13/14 vs CFA - MIDWEST WINGS 13/14 | 17 | RICE PARK | |
| 4650 | Sun 10/25 10:00am | U13/4S | YOUNG WOLVES 2013/2014 vs BLACK LIONS 13/14 | 17 | BRENT HASSERT PARK | |
| 5080* | Sun 10/25 3:30pm |
U08-5V5/5SC1 | RANGERS SOCCER ACADEMY 18/19 vs BLACK LIONS 18/19 | 35 | ALTMAN PARK | |
| 5687 | Sat 10/31 1:00pm | U08-5V5/5SC1 | CHICAGO KICS FC 18/19 BLACK CITY vs BLACK LIONS 18/19 | 25 | DUNBAR GRASS | 5 v 5 |
| 5663* | Sun 11/1 9:00am |
U13/4S | LG CELTICS 2013/2014B GREEN vs BLACK LIONS 13/14 | 17 | LYONS TOWNSHIP HS NORTH CAMPUS |