| Game Number | Date/Time | Age/Div | Teams (H vs A) | District | Field | Field Designation |
| 350 | Sat 4/11 11:00am | 12U/2S | JAKE'S STARS FC 2014 BOYS BLACK vs LTSC 2014 SELECT WHITE | 26 | KANKAKEE JUNIOR HIGH SCHOOL | |
| 2951* | Sat 4/11 4:30pm | 15U-SPRING/2S | AJAX FC NAPERVILLE 2011 RED 1 vs JAKE'S STARS FC 2011 BOYS BLACK | 17 | COMMISSIONERS PARK (NAPERVILLE) | |
| 138 | Sun 4/12 9:00am | 7U-4V4/S | JAKE'S STARS FC CUP SA 2019 vs MWGFC 2019 ELITE | 26 | KENNEDY MIDDLE SCHOOL | |
| 953 | Sun 4/12 5:00pm rainout |
19U/3S | CHICAGO EMPIRE FC SOUTH HSB II vs JAKE'S STARS FC 2007 BOYS BLACK | 17 | CAESAR PARK | 11v11 |
| 2621* | Sat 4/18 2:30pm rainout |
15U-SPRING/2S | BLACK LIONS 2011/12 vs JAKE'S STARS FC 2011 BOYS BLACK | 17 | RICE PARK | |
| 1814 | Sun 4/19 3:00pm | 16U/2S | JAKE'S STARS FC 2010 BOYS BLACK vs UESC - BSC RAIDERS 2010 BLACK | 26 | KENNEDY MIDDLE SCHOOL | |
| 2128 | Sun 4/26 9:00am | 7U-4V4/S | JAKE'S STARS FC CUP SA 2019 vs UESC-PLAINFIELD UTD 2019 SEL BLACK | 26 | KENNEDY MIDDLE SCHOOL | |
| 2319* | Sun 4/26 10:30am |
19U/3S | CHICAGO EDGE B2007/08 vs JAKE'S STARS FC 2007 BOYS BLACK | 12 | CONCORDIA UNIVERSITY CHICAGO | |
| 4420* | Sun 4/26 12:00pm |
12U/2S | LTSC 2014 SELECT WHITE vs JAKE'S STARS FC 2014 BOYS BLACK | 17 | WALKER PARK | 9v9 |
| 1094* | Sun 4/26 2:00pm | 12U/2S | INDIANA ELITE CHICAGO 2014 vs JAKE'S STARS FC 2014 BOYS BLACK | 17 | CENTRAL PARK NORTH - KENSINGTON RD. ENTRANCE | Field 9v9 left |
| 3101 | Sat 5/2 9:00am | 7U-4V4/S | ORLAND PARK STING FC 2019 vs JAKE'S STARS FC CUP SA 2019 | 66 | EAGLE RIDGE II PARK | 4v4 |
| 348* | Sat 5/2 11:00am |
16U/2S | CHICAGO CITY 2010/2011 SOUTH vs JAKE'S STARS FC 2010 BOYS BLACK | 26 | CENTENNIAL PARK (ORLAND PARK) | |
| 3345* | Sat 5/2 11:00am rainout |
12U/2S | JAKE'S STARS FC 2014 BOYS BLACK vs AYSO 300 UNITED 2014 BLUE | 26 | KENNEDY MIDDLE SCHOOL | |
| 3587 | Sun 5/3 1:00pm | 15U-SPRING/2S | JAKE'S STARS FC 2011 BOYS BLACK vs GALAXY 2011 NL | 26 | KENNEDY MIDDLE SCHOOL | |
| 7871* | Sun 5/3 1:45pm |
12U/2S | TESC 2014 SELECT 1 vs JAKE'S STARS FC 2014 BOYS BLACK | 17 | BUTTERFIELD PARK (NORTH) | |
| 3839* | Sun 5/3 4:00pm |
16U/2S | JAKE'S STARS FC 2010 BOYS BLACK vs UESC - PLAINFIELD UTD 2010 PREMIER II | 26 | KANKAKEE JUNIOR HIGH SCHOOL | |
| 3586* | Sun 5/3 5:00pm |
19U/3S | JAKE'S STARS FC 2007 BOYS BLACK vs MORRIS UNITED 2007 PREMIER | 26 | KANKAKEE HIGH SCHOOL | |
| 4152* | Sat 5/9 1:30pm |
7U-4V4/S | JAKE'S STARS FC CUP SA 2019 vs UESC - NSA 2019 RED | 26 | KENNEDY MIDDLE SCHOOL | |
| 584* | Sat 5/9 4:00pm |
15U-SPRING/2S | JAKE'S STARS FC 2011 BOYS BLACK vs TEAM CHICAGO 2011 PERFORMANCE | 26 | KANKAKEE JUNIOR HIGH SCHOOL | |
| 4551 | Sun 5/10 1:00pm | 19U/3S | JAKE'S STARS FC 2007 BOYS BLACK vs CHICAGO EMPIRE FC SOUTH HSB II | 26 | KENNEDY MIDDLE SCHOOL | |
| 4854 | Sun 5/10 4:00pm | 16U/2S | LTSC 2010 HS SHOWCASE vs JAKE'S STARS FC 2010 BOYS BLACK | 17 | LYONS TOWNSHIP HS NORTH CAMPUS | 11v11 |
| 5326* | Sat 5/16 10:00am | 12U/2S | JAKE'S STARS FC 2014 BOYS BLACK vs INDIANA ELITE CHICAGO 2014 | 26 | KENNEDY MIDDLE SCHOOL | |
| 1878* | Sat 5/16 4:30pm |
15U-SPRING/2S | CHICAGO EDGE B2011 PREMIER XI vs JAKE'S STARS FC 2011 BOYS BLACK | 12 | PRIORY PARK | |
| 4984* | Sun 5/17 8:00am | 19U/3S | CHICAGO CITY KANKAKEE vs JAKE'S STARS FC 2007 BOYS BLACK | 32 | KCSA SOCCER FIELDS | 1 |
| 5102* | Sun 5/17 1:00pm |
7U-4V4/S | JAKE'S STARS FC CUP SA 2019 vs PSG ACADEMY LEMONT 2019 | 26 | KENNEDY MIDDLE SCHOOL | |
| 5553 | Sun 5/17 1:00pm | 15U-SPRING/2S | JAKE'S STARS FC 2011 BOYS BLACK vs GLEN ELLYN LAKERS 2011 ELITE 2 | 26 | KENNEDY MIDDLE SCHOOL | |
| 5599* | Sun 5/17 2:30pm |
16U/2S | AYSO 300 UNITED 2011/10 BLUE vs JAKE'S STARS FC 2010 BOYS BLACK | 17 | SPRING ROCK PARK | |
| 6716* | Sat 5/30 3:00pm | 15U-SPRING/2S | TIGRES DC 2011 vs JAKE'S STARS FC 2011 BOYS BLACK | 7 | FOXDALE PARK | |
| 5975* | Sat 5/30 3:30pm |
12U/2S | NWI LIONS UNITED 2014 YELLOW vs JAKE'S STARS FC 2014 BOYS BLACK | 8 | NWI CHESTERTON SOCCER FIELDS | 9v9 Field #3 |
| 6219 | Sun 5/31 10:30am | 7U-4V4/S | UESC-PLAINFIELD UTD 2019 SEL WHITE vs JAKE'S STARS FC CUP SA 2019 | 66 | CLOW STEPHENS PARK | |
| 6506 | Sun 5/31 1:00pm | 19U/3S | JAKE'S STARS FC 2007 BOYS BLACK vs RUSH WEST 2007/2008 PREMIER | 26 | KENNEDY MIDDLE SCHOOL | |
| 6744 | Sun 5/31 3:00pm | 16U/2S | JAKE'S STARS FC 2010 BOYS BLACK vs NWI LIONS UNITED 2010 YELLOW | 26 | KENNEDY MIDDLE SCHOOL | |
| 2554* | Mon 6/1 6:30pm | 16U/2S | CAMPTON UNITED 2010 RED vs JAKE'S STARS FC 2010 BOYS BLACK | 14 | JAMES O BREEN COMMUNITY PARK | 18 |
| 7761* | Sat 6/6 10:00am |
16U/2S | JAKE'S STARS FC 2010 BOYS BLACK vs AYSO 300 UNITED 2011/10 BLUE | 26 | KANKAKEE HIGH SCHOOL | |
| 7277 | Sat 6/6 11:00am | 7U-4V4/S | PSG ACADEMY LEMONT 2019 vs JAKE'S STARS FC CUP SA 2019 | 66 | MT. ASSISI FIELD - DO NOT USE | 5v5, 7v7, 9v9 |
| 1163* | Sun 6/7 9:00am |
7U-4V4/S | RUSH SOUTH 2019 vs JAKE'S STARS FC CUP SA 2019 | 66 | LYONDELL PARK (MORRIS) | 4v4 |
| 7513 | Sun 6/7 1:00pm | 19U/3S | JAKE'S STARS FC 2007 BOYS BLACK vs CHICAGO CITY KANKAKEE | 26 | KENNEDY MIDDLE SCHOOL | |
| 7514 | Sun 6/7 1:00pm | 15U-SPRING/2S | JAKE'S STARS FC 2011 BOYS BLACK vs AJFC 2011 | 26 | KENNEDY MIDDLE SCHOOL | |
| 2326* | Sat 6/13 10:00am |
12U/2S | JAKE'S STARS FC 2014 BOYS BLACK vs TESC 2014 SELECT 1 | 26 | KANKAKEE JUNIOR HIGH SCHOOL | |
| 1380* | Sun 6/14 11:00am | 19U/3S | RUSH WEST 2007/2008 PREMIER vs JAKE'S STARS FC 2007 BOYS BLACK | 28 | HUMBRACHT FIELD |