| Date | Day | Time | Home Team | Away Team | Location |
| 7/1/2008 | Tuesday | 6:00PM | Irvington | Mahopac JV | Boulder Brook Park Upper |
| 7/1/2008 | Tuesday | 7:00PM | Mahopac Varsity | Hen Hud | SUNY Purchase Turf |
| 7/2/2008 | Wednesday | 6:00PM | Nanuet | Stepinac | Boulder Brook Park Upper |
| 7/2/2008 | Wednesday | 7:00PM | Sound Shore Varsity | Nor West Varsity | SUNY Purchase Turf |
| 7/2/2008 | Wednesday | 7:00PM | Putnam Valley | Brewster | Putnam Valley High |
| 7/3/2008 | Thursday | 6:00PM | Greenwich | Clarkstown South | Greenwich High |
| 7/3/2008 | Wednesday | 6:00PM | Ardsley | Eastchester | Boulder Brook Park Upper |
| 7/7/2008 | Monday | 6:00PM | White Plains Varsity | Highlanders Varsity | White Plains High |
| 7/7/2008 | Monday | 7:00PM | Mahopac Varsity | Clarkstown South | SUNY Purchase Turf |
| 7/8/2008 | Tuesday | 6:00PM | Sound Shore Varsity | Stepinac | Boulder Brook Park Upper |
| 7/9/2008 | Wednesday | 6:00PM | White Plains Varsity | Greenwich | White Plains High |
| 7/9/2008 | Wednesday | 6:00PM | Nanuet | Irvington | Boulder Brook Park Upper |
| 7/9/2008 | Wednesday | 7:00PM | Putnam Valley | Highlanders Varsity | Putnam Valley High |
| 7/9/2008 | Wednesday | 7:00PM | Hen Hud | Fordham Prep | SUNY Purchase Turf |
| 7/10/2008 | Thursday | 6:00PM | Greenwich | Brewster | Greenwich High |
| 7/10/2008 | Thursday | 6:00PM | Nor West Varsity | Ardsley | Boulder Brook Park Upper |
| 7/10/2008 | Thursday | 7:00PM | Mahopac JV | Eastchester | SUNY Purchase Turf |
| 7/15/2008 | Tuesday | 6:00PM | Sound Shore Varsity | Irvington | Boulder Brook Park Upper |
| 7/15/2008 | Tuesday | 7:00PM | Nor West Varsity | Mahopac JV | SUNY Purchase Turf |
| 7/16/2008 | Wednesday | 6:00PM | White Plains Varsity | Hen Hud | White Plains High |
| 7/16/2008 | Wednesday | 6:00PM | Nanuet | Eastchester | Boulder Brook Park Upper |
| 7/16/2008 | Wednesday | 7:00PM | Clarkstown South | Fordham Prep | SUNY Purchase Turf |
| 7/17/2008 | Thursday | 6:00PM | Greenwich | Highlanders Varsity | Greenwich High |
| 7/17/2008 | Thursday | 6:00PM | Ardsley | Stepinac | Boulder Brook Park Upper |
| 7/21/2008 | Monday | 7:00PM | Mahopac Varsity | Putnam Valley | SUNY Purchase Turf |
| 7/22/2008 | Tuesday | 6:00PM | Sound Shore Varsity | Eastchester | Boulder Brook Park Upper |
| 7/22/2008 | Tuesday | 7:00PM | Nanuet | Nor West Varsity | SUNY Purchase Turf |
| 7/23/2008 | Wednesday | 6:00PM | White Plains Varsity | Clarkstown South | White Plains High |
| 7/23/2008 | Wednesday | 7:00PM | Putnam Valley | Hen Hud | Putnam Valley High |
| 7/23/2008 | Wednesday | 7:00PM | Mahopac JV | Stepinac | SUNY Purchase Turf |
| 7/24/2008 | Thursday | 6:00PM | Greenwich | Fordham Prep | Greenwich High |
| 7/24/2008 | Thursday | 6:00PM | Ardsley | Irvington | Boulder Brook Park Upper |
| 7/24/2008 | Thursday | 7:00PM | Mahopac Varsity | Highlanders Varsity | John Jay High |
| 7/24/2008 | Thursday | 8:00PM | Brewster | Fordham Prep | John Jay High |
| 7/28/2008 | Monday | 7:00PM | Highlanders Varsity | Fordham Prep | SUNY Purchase Turf |
| 7/28/2008 | Monday | 8:00PM | Greenwich | Hen Hud | SUNY Purchase Turf |
| 7/29/2008 | Tuesday | 6:00PM | Sound Shore Varsity | Nanuet | Boulder Brook Park Upper |
| 7/29/2008 | Tuesday | 7:00PM | Ardsley | Mahopac JV | SUNY Purchase Grass |
| 7/29 /2008 | Tuesday | 7:00PM | Mahopac Varsity | Brewster | SUNY Purchase Turf |
| 7/30/2008 | Wednesday | 6:00PM | White Plains Varsity | Brewster | White Plains High |
| 7/30/2008 | Wednesday | 6:00PM | Irvington | Eastchester | Boulder Brook Park Upper |
| 7/30/2008 | Wednesday | 7:00PM | Putnam Valley | Clarkstown South | Putnam Valley High |
| 7/30/2008 | Wednesday | 7:00PM | Nor West Varsity | Stepinac | SUNY Purchase Turf |