| TBD | Dick's Sporting Goods Discount Days (both Lexington locations) |
| Feb 14, 2026 (9am-12pm) | Majors/Minors Tryout 1 @ Champions Sports (2061 Lexington Road, Nicholasville, KY) |
| Feb 21, 2026 (9:30am-1:30pm) | Rookie Evaluations @ The Yard (117 Westhampton Dr, Lexington, KY 40511) |
| Feb 22, 2026 (3pm-7pm) | Majors/Minors Tryout 2 @ Champions Sports (2061 Lexington Road, Nicholasville, KY) |
| TBD | Dick's Sporting Goods Discount Days (both Lexington locations) |
| March 7, 2026 | Park Cleanup Day |
| March 16, 2026 | Major Division Games begin |
| March 26, 2026 | Minor Division Games begin |
| March 28, 2026 | Opening Day Ceremony/Rookie Division Games begin |
| Mid-April, 2026 | Tee Ball & Wee Ball Games begin |
| April 18, 2026 | Opening Day Ceremony (rain date) |
| April 25, 2026 | ELL Night at Lexington Legends Game |
| TBD (May) | Picture Day |
| May 10, 2026 | Mother's Day |
| May 15, 2026 | Light 'Em Up Fundraiser |
| May 16, 2026 | All-Star/Turkey Feet Tryouts (5yo-6yo) |
| May 17, 2026 | All-Star/Turkey Feet Tryouts (7yo-8yo) |
| May 25, 2026 | Memorial Day (no scheduled games) |
| May 30 - June 6, 2026 | End of Season Tournament (Tee Ball, Rookie, Minors & Majors) |
| June 6, 2026 | League Championship Games (Tee Ball, Rookie, Minors & Majors) |
| June 6, 2026 | Season Closing Picnic and Award Ceremonies & Home Run Derby |
| June 7, 2026 | Announcement of All-Star Teams |
| June 20-24, 2026 | Coach Pitch (League Ages 7-8) District Tournament (Richmond, KY) |
| June 27 - July 1, 2026 | Little League (League Ages 9-12) District Tournament (Bluegrass LL - Lexington, KY) |
| July 1, 2026 | Fall Season Registration Opens |
| July 11-15, 2026 | Coach Pitch (League Ages 7-8) State Tournament (Richmond, KY) |
| July 18-22, 2026 | Little League (League Ages 9-12) State Tournament (Grayson, KY) |