| Event/Meet | Date | Location |
| Fall Coaches' Meeting | October 2, 1968 | Auburn High School |
| Varsity I | November 6, 1968 | Anna Maria College |
| Varsity II | January 8, 1969 | Worcester North High School (North) and Marianhill High School (South) |
| Varsity III | March 5, 1969 | Shrewsbury High School (North) and Quaboag Regional Middle/High School (South) |
| Varsity IV | May 7, 1969 | Tantasqua Regional High School (North) and Marianapolis Preparatory School (South) |