Principal's Prize
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Also known as the Headteacher's Award, this was presented for the first time in 2012. The award in 2009 was during the "Boston Grammar Schools Federation" and may have been a Boston High School prize.
The reason given for the creation of the prize was that, from 1 January 2013, Boston Grammar School would become Boston Grammar School Academy and that the head of an academy is known as a principal. The headmaster, then Paul Marsh, would therefore be known as the "Principal" from that date,
| Year | Winner |
|---|---|
| 2009 | Naomi Shaw |
| ... | |
| 2012 | Aidan McClure |
| 2013 | ? |
| 2014 | Vashist Motkur |