| Tuesday, May 21 |
| MINOR |
| Highland Mets MINOR @ Highland Cardinals MINOR | 5:30pm | Highland - Major Field |
| Highland Reds MINOR @ Highland Rockies MINOR | 7:00pm | Highland - Major Field |
| Tee Ball - Pitching Machine |
| Bees @ Hooks | 5:30pm | Highland - Lower Field |
| Bats @ Rock Hounds | 6:45pm | Highland - Lower Field |
| Wednesday, May 22 |
| MAJOR |
| Highland White (Carter) @ JKL Construction(Hopple-red) | 5:30pm | Golfmoor |
| Highland Navy (Neumann) @ Highland Grey (Fisher) | 5:30pm | Highland - Major Field |
| ROOKIE |
| Rockies - Rookie @ Reds - Rookie | 5:30pm | Highland - Lower Field |
| Pirates - Rookie @ Cubs - Rookie | 7:00pm | Highland - Lower Field |
| Thursday, May 23 |
| MINOR |
| Highland Cardinals MINOR @ Highland Reds MINOR | 5:30pm | Highland - Major Field |
| Highland Giants MINOR @ Highland Cubs MINOR | 7:00pm | Highland - Major Field |
| Tee Ball - Pitching Machine |
| Rattlers @ Storm | 5:30pm | Highland - Lower Field |
| Grass Hoppers @ Bulls | 6:45pm | Highland - Lower Field |
| Tee Ball - Only |
| Mets - T-Ball Only @ Cubs - T-Ball Only | 5:30pm | Highland - Pony Field |
| Cardinals - T-Ball Only @ Dodgers - T-Ball Only | 6:30pm | Highland - Pony Field |
| Friday, May 24 |
| ROOKIE |
| Mets - Rookie @ Cardinals - Rookie | 5:30pm | Highland - Lower Field |
| Giants - Rookie @ Pirates - Rookie | 7:00pm | Highland - Lower Field |
| Tuesday, May 28 |
| MINOR |
| Highland Giants MINOR @ Highland Reds MINOR | 5:30pm | Highland - Major Field |
| Highland Cubs MINOR @ Highland Cardinals MINOR | 7:00pm | Highland - Major Field |
| ROOKIE |
| Cubs - Rookie @ Mets - Rookie | 5:30pm | Highland - Lower Field |
| Mets - Rookie @ Rockies - Rookie | 7:00pm | Highland - Lower Field |
| Wednesday, May 29 |
| MAJOR |
| MV White-Expressway Chevrolet @ Highland Navy (Neumann) | 5:30pm | Highland - Major Field |
| Highland Red (Cullen) @ Highland Grey (Fisher) | 7:30pm | Highland - Major Field |
| MINOR |
| Highland Rockies MINOR @ Golfmoor Pfister - Black | 7:00pm | Golfmoor |
| ROOKIE |
| Reds - Rookie @ Pirates - Rookie | 5:30pm | Highland - Lower Field |
| Giants - Rookie @ Cardinals - Rookie | 7:00pm | Highland - Lower Field |
| Tee Ball - Pitching Machine |
| Rattlers @ Bees | 5:30pm | Highland - Pony Field |
| Rock Hounds @ Grass Hoppers | 6:45pm | Highland - Pony Field |
| Thursday, May 30 |
| MAJOR |
| MV Gray-Shephard Services @ Highland Navy (Neumann) | 7:30pm | Highland - Major Field |
| MINOR |
| Highland Mets MINOR @ Highland Rockies MINOR | 5:30pm | Highland - Major Field |
| Tee Ball - Only |
| Mets - T-Ball Only @ Cardinals - T-Ball Only | 5:30pm | Highland - Pony Field |
| Dodgers - T-Ball Only @ Cubs - T-Ball Only | 6:30pm | Highland - Pony Field |
| Friday, May 31 |
| MAJOR |
| MV Gray-Shephard Services @ Highland White (Carter) | 5:30pm | Highland - Major Field |
| Highland Red (Cullen) @ MV Black-Complete Game Academy | 5:30pm | Mt. Vernon |
| MV Maroon-McKim's IGA @ Highland Grey (Fisher) | 7:30pm | Highland - Major Field |
| MINOR |
| Highland Giants MINOR @ Golfmoor Paul - Green | 5:15pm | Golfmoor |
| Highland Reds MINOR @ Golfmoor Carlton - Navy Blue | 7:00pm | Golfmoor |
| ROOKIE |
| Cardinals - Rookie @ Reds - Rookie | 5:30pm | Highland - Lower Field |
| Cubs - Rookie @ Giants - Rookie | 7:00pm | Highland - Lower Field |
| Tee Ball - Pitching Machine |
| Bulls @ Hooks | 5:30pm | Highland - Pony Field |
| Bats @ Storm | 6:45pm | Highland - Pony Field |
| Saturday, Jun 1 |
| MAJOR |
| Highland Grey (Fisher) @ MV White-Expressway Chevrolet | 2:00pm | Mt. Vernon |
| Highland White (Carter) @ MV Graphite-Consolidated Grain & Barge | 4:00pm | Mt. Vernon |
| MINOR |
| Highland Reds MINOR @ Golfmoor Paulin - Purple | 9:00am | Golfmoor |
| Mt Vernon - Maroon @ Highland Cardinals MINOR | 9:00am | Highland - Major Field |
| Golfmoor Paul - Green @ Highland Rockies MINOR | 11:00am | Golfmoor |
| Mt Vernon - Black @ Highland Cubs MINOR | 11:00am | Highland - Major Field |
| Highland Giants MINOR @ Golfmoor Carlton - Navy Blue | 1:00pm | Golfmoor |
| Mt Vernon - Gray @ Highland Mets MINOR | 1:00pm | Highland - Major Field |
| ROOKIE |
| Rockies - Rookie @ Cubs - Rookie | 2:00pm | Highland - Lower Field |
| Reds - Rookie @ Giants - Rookie | 3:30pm | Highland - Lower Field |
| Cardinals - Rookie @ Pirates - Rookie | 5:00pm | Highland - Lower Field |
| Tee Ball - Pitching Machine |
| Rattlers @ Grass Hoppers | 9:00am | Highland - Lower Field |
| Bees @ Rock Hounds | 10:15am | Highland - Lower Field |
| Bulls @ Storm | 11:30am | Highland - Lower Field |
| Hooks @ Bats | 12:45pm | Highland - Lower Field |
| Tee Ball - Only |
| Cubs - T-Ball Only @ Cardinals - T-Ball Only | 9:00am | Highland - Pony Field |
| Mets - T-Ball Only @ Dodgers - T-Ball Only | 10:00am | Highland - Pony Field |
| Monday, Jun 3 |
| ROOKIE |
| POSITION/TBD @ Cardinals - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Cubs - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Giants - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Mets - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Pirates - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Reds - Rookie | 5:30pm | Highland - Lower Field |
| POSITION/TBD @ Rockies - Rookie | 5:30pm | Highland - Lower Field |
| Tee Ball - Pitching Machine |
| Rattlers @ Rock Hounds | 5:30pm | Highland - Pony Field |
| Bees @ Grass Hoppers | 6:45pm | Highland - Pony Field |
