The school presents two Headteacher Awards each year. The Headmaster’s Cup is a prestigious prize presented to the senior student who has demonstrated a substantial contribution during his time at the school. It is chosen by the Co-Headteachers and presented at the Senior Awards Evening. Since 2014, the school has presented the Headteacher’s Cup. This trophy is specifically for students in Years 7-9 that have shown outstanding attainment and progress during their first three years in the school. The full list is below.
| Year | Headteacher’s Cup (Junior) | Headmaster’s Trophy (Senior) |
|---|---|---|
| 2001-02 | Not awarded | |
| 2002-03 | Not awarded | |
| 2003-04 | Not awarded | |
| 2004-05 | Not awarded | |
| 2005-06 | Not awarded | Darren West |
| 2006-07 | Not awarded | Darren West |
| 2007-08 | Not awarded | Kivraj Sabarwal |
| 2008-09 | Not awarded | Michael Kettle |
| 2009-10 | Not awarded | |
| 2010-11 | Not awarded | |
| 2011-12 | Not awarded | Charles Greaves |
| 2012-13 | Not awarded | Dejan Butler |
| 2013-14 | Harry Stenholm | Max Mills |
| 2014-15 | Tom Keenan | Josh Norris |
| 2015-16 | John Alvaran | Louis Kelly |
| 2016-17 | Lars-Leander Volle | Maxwell Omondi |
| 2017-18 | Ben Rawsthorne | Gheorghe Rotaru |
| 2018-19 | Matthew Nunan | Daniel Ashton |
| 2019-20 | Oliver Hone | Diallo Williams |
| 2020-21 | Kaname Asaki | Morgan Lawrence |
| 2021-22 | Max Manson | Ben Rawsthorne |
| 2022-23 | Jonas Canniere | Matthew Nunan |
| 2023-24 | Sam Gilmour | To be awarded December 2024 |