| Event/Meet | Date | Location |
| Fall Coaches' Meeting | September 10, 2008 | St. John's High School |
| Varsity I | October 8, 2008 | Shrewsbury High School (A & C) and Tahanto Regional High School (B & D) |
| Freshman I | November 5, 2008 | Wachusett Regional High School |
| Varsity II | December 3, 2008 | Auburn High School (A & C) and Douglas High School (B & D) |
| Freshman II | January 14, 2009 | Wachusett Regional High School |
| Varsity III | February 4, 2009 | Shrewsbury High School (A & C) and Leicester High School (B & D) |
| Massachusetts ARML Tryouts | March 1, 2009 | Worcester Academy, Phillips Academy Andover, and Lexington High School |
| Varsity IV | March 4, 2009 | Wachusett Regional High School (A & B & C & D) |
| Freshman III | March 25, 2009 | Wachusett Regional High School |
| Massachusetts State Championship Math Meet | April 3, 2009 | Shrewsbury High School |
| New England Championship Math Meet | May 1, 2009 | Canton High School |
| Spring Coaches' Meeting | May 6, 2009 | Worcester Academy |