Hugo followed suit, successfully navigating a combine in spring this year. He has started his A-levels and is enjoying all academic and sporting aspects. Being ‘Academy men’ has involved playing opportunities in Europe and in the States, as well as a regular October fixture at the Tottenham Hotspur Stadium. Aside from the Academy, both have represented GB U17.
Austin is keen to emulate his big brothers, currently playing Flag Football (the non-contact version) with Solent Spitfires. He’d like to make the move to contact soon.
It goes without saying that the prep school education the boys received at Pilgrims’ provided excellent preparation for them, from the rigorous work ethic of choristership, to boarding, to sport, to academics.
I am enjoying my new Deputy Head Co-Curriculum role at Sherborne Jeddah in Saudi Arabia. We are in our founding year, which makes it an exciting and rewarding prospect. Currently, we educate children from Nursery to Year 7 but will grow through to A-levels in time. Saudis are very welcoming, and I have spent my weekends open water swimming, hiking and learning to sail!
Meanwhile, Emma maintains our strong links with Pilgrims’ as she stays in Winchester with Austin and continues in her roles as Registrar and PE teacher. I’m thrilled she is currently on her second trip to Saudi to see me, before we head home together in time for the festive break.
The boys and I miss Pilgrims’ and think fondly of the strong community, especially at times like Christmas.
Andrew Short
Ex-Director of Sport and Main School Housemaster
(Published: 10/12/2025)

The Pilgrims' School, Winchester
Outstanding prep school in Winchester for boys aged 4-13, day and boarding.
Think you’ve seen everything that happens at Pilgrims’? Think again… 🎉
We’re starting our summer highlights series with our incredible #Athletics Finals Day, and what a day it was. With our Prep boys taking to our incredible Wolvesey Castle fields the boys put on a show, with a number of new school records too. Well done, boys! 🏃
What highlight is coming next? 🤔
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Yesterday, we said goodbye to our incredible leavers. 💚
We are so incredibly proud of each and every one of them and everything they’ve achieved during their time here at Pilgrims’. It has been a privilege to watch them grow, learn and flourish, and we know they have bright futures ahead.
We’d like to wish all of our leavers and their families the very best as they embark on their next adventure.
But don’t worry… this isn’t the last you’ll see of them! 👀✨
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🎨 Art and DT exhibition 🪚
Tonight saw the culmination of the work by our boys in Art and DT. With some truly staggering work on display the boys have showed amazing discipline, creativity and resilience which can certainly be seen in the final product.
A big thank you to our Art teacher, Ros Priddle and our DT teacher Any Herbert who have inspired the boys and curated tonight’s exhibition.
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