Two-Time Champions
| Student | School | Years |
|---|---|---|
| Dhroova Aiylam | St. John's / Mass Academy | 2010-11, 2012-13 |
| Rahul Banerjee | St. John's | 2002-03, 2004-05 |
| Chia-Hao Yu | Worcester Academy | 1993-94, 1994-95 |
| Edward Hanson | St. John's | 1991-92, 1992-93 |
| Arthur Kalb | St. John's | 1985-86, 1986-87 |
| David Glazer | Shrewsbury | 1974-75, 1976-77 |