| Event/Meet | Date | Location |
| Fall Coaches' Meeting | September 11, 2013 | Worcester Academy |
| Varsity I | October 9, 2013 Snow date: October 23, 2013 |
Shrewsbury High School (A) and Wachusett Regional High School (B & C & D) |
| Freshman/JV I | October 30, 2013 Snow date: November 6, 2013 |
Douglas High School |
| Varsity II | November 20, 2013 Snow date: December 4, 2013 |
Shrewsbury High School (A) and Auburn High School (B & C & D) |
| Freshman/JV II | December 11, 2013 Snow date: December 18, 2013 |
Worcester North High School |
| Varsity III | January 8, 2014 Snow date: January 29, 2014 |
Worcester North High School (A) and Montachusett Regional Vocational Technical School (B & C & D) |
| Freshman/JV III | February 12, 2014 Snow date: March 5, 2014 |
South High Community School |
| Varsity IV | February 26, 2014 Snow date: February 27, 2014 |
Wachusett Regional High School (A & B & C & D) |
| Spring Coaches' Meeting | April 2, 2014 | Worcester Academy |
| Massachusetts State Championship Math Meet | April 4, 2014 | Shrewsbury High School |
| New England Championship Math Meet | May 2, 2014 | Canton High School |