Old Oswestrians

1882: The very first Old Oswestrian Dinner takes place, bringing former pupils together in celebration of shared memories and lifelong friendships. This gathering marks the birth of the Old Oswestrian Society – a tradition that continues to unite generations of alumni.

Why we exist

To develop and strengthen ties between Old Oswestrians and Oswestry School by providing diverse tangible benefits including career services, networking opportunities, special events and lectures, and the opportunity to connect with and inspire pupils and graduates.

The Old Oswestrians work together to develop and improve lifelong relationships between the School, former pupils and staff. The Old Oswestrian Society is at the heart of that extended family and aims to help OOs maintain contact with their friends, teachers and the School, as well as making the most of Oswestry connections for their work and career development.

The Old Oswestrian Committee is the heart of the alumni network - a dedicated group of volunteers working to keep the spirit of Oswestry School alive long after leaving. Representing a diverse mix of generations, professions, and passions, the committee champions connection, supports school initiatives, and helps shape events, mentorship opportunities, and communications for the OO community.

Whether organising Founder’s Day, guiding alumni projects, or fostering lifelong friendships, the committee is here to ensure every Old Oswestrian feels part of something lasting and meaningful.

Oswestry Connect

Are you an Old Oswestrian? Have you joined Oswestry Connect yet?

Oswestry Connect is the official alumni network of Oswestry School, designed to keep Old Oswestrians and the wider school community connected. 

  • Reconnect with classmates and staff
  • Access news, events, and photo galleries
  • Share personal and professional updates
  • Explore career development and mentoring opportunities
  • Promote businesses and charitable causes

Whether you're seeking to rekindle old friendships, expand your professional network, or stay informed about school developments, Oswestry Connect offers a vibrant community to support and inspire you.

Join the network today and continue your lifelong connection with Oswestry School.

Oswestry Connect

Beyond the Gate

One of the greatest strengths of the Old Oswestrian network is its willingness to give back. The Mentoring & Work Experience Programme connects recent leavers with alumni who can offer guidance, insight, and real-world opportunities.

Whether it’s a conversation over coffee, a CV review, or a placement in a professional setting, this programme helps bridge the gap between education and career. It’s about sharing experiences, opening doors, and helping the next generation of OOs find their path with confidence.

If you're an alumnus looking to offer support this is where meaningful connections begin.

Events

The Old Oswestrian Events Calendar is your go-to guide for reunions, networking evenings, Founder’s Day celebrations, sports fixtures, and more. Whether you're looking to reconnect with classmates, grow your professional network, or simply enjoy a great evening out, there’s something here for every Old Oswestrian. 

Cheltenham Cricket Festival

Join Us for an Exclusive Hospitality Experience at the Cheltenham Cricket Festival!

Cheltenham College, College Sports Ground, Cheltenham

Wednesday 23 Jul 2025

9:00 AM - 6:00 PM 

Find out more and book tickets

Founder’s Day and Old Oswestrian Dinner 2025

Saturday 13 September 2025

9:00 AM – 11:30 PM

Celebrate the rich heritage of Oswestry School and the enduring spirit of the Old Oswestrian community at our much-anticipated Founder’s Day 2026. Whether you're reconnecting with old friends or introducing family to the school’s vibrant traditions, the day promises something for everyone!

Find out more

 
 

Past Events

 

Take a look back at some of our favourite moments — reunions, celebrations, and connections captured through the years.

 

News

Stay in the loop with the latest from the Oswestry School community. From alumni achievements and school milestones to event highlights and inspiring stories from around the globe, this is your hub for all things Old Oswestrian. Whether you’re near or far, these stories keep you connected to the people, memories, and moments that make Oswestry so special.

Read about what's new with OOs

Related Stories

More Stories
More Stories

Welcome to the Digital Archive of The Oswestrian

We are proud to present digital editions of The Oswestrian, the official magazine chronicling the vibrant life and achievements of Oswestry School. This online collection offers readers instant access to past and present issues, preserving our heritage while embracing the ease of modern technology. Whether you're an Old Oswestrian, current pupil, parent, or friend of the school, explore these pages to revisit treasured memories, discover school milestones, and celebrate the enduring spirit of our community—anytime, anywhere.

2016-172017-182018-192019-202023-24
What is the Old Oswestrian Society (OOS)?

The OOS is the alumni network for former pupils of Oswestry School, created to foster lifelong connections, support the school community, and celebrate shared heritage.

How can I update my contact details?

You can update your information by contacting the alumni office or logging into the Oswestry Connect platform.

How do I get involved with OOS events or reunions?

Check our Events Calendar on Oswestry Connect to stay informed about upcoming gatherings, Founder’s Day, and more.

Can I volunteer or become a mentor?

Absolutely! We're always looking for OOs willing to share their time, experience, or advice with current pupils and recent leavers. Email [email protected] to learn more.

How can I share news or achievements with the OOS community?

We’d love to hear from you. Submit your updates via the News section on Oswestry Connect or email [email protected] to be featured in the next magazine or spotlight.

How is the OOS committee involved?

The committee helps organise events, guide initiatives, and ensure the society stays vibrant and inclusive. If you would like more information on how to join please email [email protected].

How can I support Oswestry School as an alumnus?

You can contribute your time, expertise, or philanthropic support to help pupils today and in the future. For more information email [email protected].

More in...

Community