| Event/Meet | Date (All Events Start at 3:15 PM) | Location |
| Fall Coaches' Meeting | Sep 12, 2018 | Auburn High School |
| Varsity I | Oct 03, 2018 Snow date: Oct 10, 2018 |
Shrewsbury High School (A) and Wachusett Regional High School (B, C, D, & V) |
| Varsity II | Nov 28, 2018 Snow date: Dec 05, 2018 |
Shrewsbury High School (A) and Wachusett Regional High School (B, C, D, & V) |
| Varsity III | Jan 23, 2019 Snow date: Jan 30, 2019 |
Westborough High School (A) and Assabet Valley Regional Technical High School (B, C, D, & V) |
| Varsity IV | Feb 27, 2019 Snow date: Mar 06, 2019 |
Westborough High School (A) and Assabet Valley Regional Technical High School (B, C, D, & V) |
| Freshman/JV I | Oct 24, 2018 Snow date: Oct 31, 2018 |
Assabet Valley Regional Technical High School |
| Freshman/JV II | Dec 12, 2018 Snow date: Dec 19, 2018 |
Assabet Valley Regional Technical High School |
| Freshman/JV III | Mar 13, 2019 Snow date: Mar 20, 2019 |
Wachusett Regional High School |
| Spring Coaches' Meeting | Apr 24, 2019 | Massachusetts Academy of Math and Science |