| Game # | Date | Start Time | Home | Visitor | Diamond |
| 1 | 08/07/2026 | 6:00 PM | Milton Blue Jays | HH - Dodgers | Trafalgar Sports Park - 3 |
| 3 | 08/07/2026 | 8:00 PM | Milton Yankees | Milton A's | Trafalgar Sports Park - 3 |
| 2 | 08/07/2026 | 8:30 PM | HH - Yankees | Milton Red Sox | Georgetown Fairgrounds Diamond 1 |
| 4 | 08/08/2026 | 10:00 AM | HH - Yankees | HH - Dodgers | Trafalgar Sports Park - 3 |
| 5 | 08/08/2026 | 10:00 AM | Milton Blue Jays | Milton A's | Georgetown Fairgrounds Diamond 1 |
| 6 | 08/08/2026 | 12:30 PM | Milton Yankees | Milton Red Sox | Trafalgar Sports Park - 3 |
| 7 | 08/08/2026 | 3:00 PM | Milton Blue Jays | HH - Yankees | Trafalgar Sports Park - 3 |
| 8 | 08/08/2026 | 3:00 PM | Milton Yankees | HH - Dodgers | Georgetown Fairgrounds Diamond 1 |
| 9 | 08/08/2026 | 5:30 PM | Milton A's | Milton Red Sox | Trafalgar Sports Park - 3 |
| 12 | 08/09/2026 | 10:00 AM | Semi (1st vs 4th) | Semi (1st vs 4th) | Trafalgar Sports Park - 3 |
| 13 | 08/09/2026 | 10:00 AM | Semi (2nd vs 3rd) | Semi (2nd vs 3rd) | Georgetown Fairgrounds Diamond 1 |
| 15 | 08/09/2026 | 12:30 PM | Final | Final | Trafalgar Sports Park - 3 |