Find out more
We are thrilled to announce that Tim Head, our Deputy Director of Admissions and Marketing, has been named the winner of the Stephen Winkley Award at the 2025 Boarding Schools’ Association (BSA) Supporting Excellence Awards.
The awards were announced at the BSA Annual Conference for Heads, sponsored by Schoolblazer, held at York Racecourse on 6–7 May 2025. With a record number of entries submitted across 14 categories, this year’s awards saw more than 300 nominations and just 45 shortlisted.
The Stephen Winkley Award was the final category to be announced and commends the achievements of an individual who has made a significant contribution to the cause of boarding. It is BSA’s longest-running award, given in memory of Stephen Winkley, former BSA Chair (2003), and Headmaster of Uppingham (1991–2006) and Rossall Schools (2008–2013). The presentation was made particularly special by being delivered by Stephen Winkley’s son, Leo Winkley, Head of Shrewsbury School.
Tim’s contribution to Wellington College and the wider boarding community over the last 39 years was described by judges as “truly inspiring.” They added: “His commitment to all things boarding, as a housemaster, in admissions, and through many other duties, across 114 terms over 39 years is truly inspiring. Generations of boarders, literally, have benefitted from his warm pastoral care and support, which is what great boarding is all about.”
Tim began his career at Wellington as an English teacher in 1986 and has since shaped College life through countless roles: Housemaster of Beresford, tutor, coach of cricket and hockey, golf supporter, Yearbook editor, CCF officer, and Arts Committee member. His legacy is built on personal connection and tireless advocacy for the boarding experience.
“Tim Head lives and breathes Wellington – an inspiring English teacher, a compassionate and caring Housemaster, and one of the strongest advocates for a boarding education,” shared Phil Mann, Director of Admissions.
Pupils, colleagues and alumni were delighted by Tim’s recognition. William (10 Bl) shared: “His nomination for this award is absolutely fitting as he is an amazing tutor, and someone who has given so much back to our community. I understand this may seem silly, but his contributions and support for my wellbeing and academics are something that I appreciate more than I can put into words.”
Sam Owen, Housemaster of the Blücher, echoed the sentiment: “In an age where it is too easy to get lost in box ticking, form-filling, and project managing, Tim is all about the individual.”
Angus Paskin Orr (Bd 2010) recalled: “The Beresford was a house full of strong characters – not always the easiest bunch – but Tim handled us with patience, humour, and a deep understanding of what made each of us tick. On the rare occasions when challenges arose, Tim was exceptionally supportive.”
Ed Young (Bd 2007) added: “He struck the right balance between letting us be teenagers and keeping us in line. I learnt a lot from him and always appreciated his support.”
We are incredibly proud of Tim and of all our staff and students who continue to drive inclusion and excellence in our boarding community. Our heartfelt thanks go to the BSA for recognising these efforts, and congratulations to all fellow finalists and winners this year.
