| Event/Meet | Date | Location |
| Fall Coaches' Meeting | September 15, 1999 | Tahanto Regional High School |
| Varsity I | October 13, 1999 | Assabet Valley Regional Technical High School |
| Freshman I | November 3, 1999 | Algonquin Regional High School |
| Varsity II | December 1, 1999 | Shrewsbury High School |
| Freshman II | January 12, 2000 | Westborough High School |
| Varsity III | February 2, 2000 | Assabet Valley Regional Technical High School |
| Freshman III | March 1, 2000 | Doherty Memorial High School |
| Varsity IV | April 5, 2000 | Bartlett High School |
| Spring Coaches' Meeting | May 3, 2000 | Worcester Academy |