| July 21 - 28 | Germany International Tour to LAOLA Cup | | | |
| August 6 | 2018-10 Boys and Girls Tryouts (CITY) | | | |
| 2018-10 Boys and Girls Tryouts (SOUTH) | | | |
| August 14 - 17 | Fall Pre-Spring Outdoor Competitive Camp | | | |
| August 15 | 2023/24 Fall Kick Off Orientation Zoom Meeting | | | |
| August 18 - 20 | Presidents Cup Play in Rockford | | | |
| August 21 - November 12 | Fall Outdoor Season | | | |
| August 21 | HS Girls Season Begins | | | |
| August 28 | 2023/24 Club Season Begins: 7U-15U Teams | | | |
| September 4 | Labor Day Holiday - No Practices | | | |
| September 5 - 10 | Fall Grassroots Programming Starts (Toddlers/Juniors) | | | |
| September 10 | Juniors Fall Festival (1 of 4) | | | |
| September 17 | Juniors Fall Festival (2 of 4) @TESC | | | |
| September 22 - 24 | Glen Ellyn Lakers Fall Classic (Tournament) | | | |
| September 23 | Chicago Fire Club Outing (Hispanic Heritage Night) vs. New England Revolution (7:30PM KO) | | | |
| September 29 - October 1 | Socctoberfest (Tournament) | | | |
| September 30 | Chicago Red Stars - Team Outing vs. Racing Louisville FC (7PM KO) | | | |
| October 1 | Juniors Fall Festival (3 of 4) @CELTICS | | | |
| October 6 - 8 | Libertyville Octoberfest Classic (Tournament) | | | |
| October 8 | HS Boys - Supplemental Tryouts (City/North, 6:30-8p) | | | |
| October 11 - 15 | Fall Grassroots Programming Ends (Toddlers/Juniors) | | | |
| October 15 | Juniors Fall Festival (4 of 4) @KICS | | | |
| October 15 | Comer 5K Run Fundraiser (8-11AM) | | | |
| October 15 | HS Boys - Supplemental Tryouts (City/North, 6:30-8p) | | | |
| October 20 - 22 | CSA Kick or Treat (Tournament) | | | |
| October 22 | Presidents Cup Semifinals & Finals Rockford | | | |
| October 31 | Halloween Day - No Practices | | | |
| November 3 - 5 | SLSG Girls Fall Classic (Tournament Showcase) | | | |
| November 11 - 12 | Raptors Veterans Day Classic (Tournament Showcase) | | | |
| November 12 | Fall Season Ends | | | |
| November 13 - 26 | Thanksgiving Off | | | |
| November 14 | 2023/24 Winter Kick Off Orientation Zoom Meeting | | | |
| November 27 - December 17 | Winter I Indoor Season (3 weeks) | | | |
| November 27 - December 1 | Placement Week (HS Boys Teams) | | | |
| December 17 | Last Day of Practice - Before Winter Break | | | |
| January 8 - March 17 | Winter II Indoor Season (10 weeks) | | | |
| February 15 | State/Pres/IL Cup Payment Reminder | | | |
| February 17-18 | Presidents Day Tournament | | | |
| February 19 | President Day - No Practices | | | |
| February 23-25 | Las Vegas Mayor's International Showcase (HS Girls Teams) | | | |
| March 6 | 2023/24 Spring Kick Off Orientation Zoom Meeting | | | |
| March 8-10 | Region Cup College Showcase (HS Boys Teams) | | | |
| March 17 | End Of Winter Indoor Season | | | |
| March 18 - 20 | Spring Pre-Spring Outdoor Competitive Camp | | | |
| March 30 | Chicago Easter Egg Hunt | | | |
| March 31 | Easter Sunday - No Games | | | |
| April 1 - June 9 | Spring Outdoor Season | | | |
| April 26 | Annual Community Clean & Green (Earth Day) | | | |
| May 6 - 9 | Girls & Boys Tryouts (8U-14U Age Groups) | | | |
| May 18-19 | Girls High School Tryouts (15-19U Age Groups) | | | |
| May 24 - 27 | Memorial Day Tournament Weekend | | | |
| May 27 | Memorial Day - No Practices | | | |
| June 7 | Last Spring Practice | | | |
| June 7 | Night of Champions - End of Season Awards & College Night/Senior Appreciation | | | |
| June 8 | Boys High School Tryouts (15-19U Age Groups) | | | |
| June 8 - 9 | Spring Season Ends | | | |
