Friday 23 May 2025: Marking the 100th anniversary of the official opening of the Memorial Gateway. From left to right: Messrs Larry Moser & Peter van Schalkwyk (WBHS Deputy Heads), Deon Scheepers (WBHS Headmaster), Cedric Poleman (WBJS Headmaster), and Grantley Rhode (WBJS Deputy Head). WBHS Piper, Nicholas Mundy.
It's been a busy period for the Union and the Schools since we last communicated by email from Gqeberha on the eve of the annual Wynberg Grey Weekend. Both schools and our Old Boys' Golf acquitted themselves well, with the highlight of the weekend, the WBHS 1st XV rugby win against Grey High on The Kolisi Field.
What a time to be part of this brotherhood. From catching up at our first London reunion in over a decade, to cheering on our Old Boys to wins in the Varsity Cup and ICC Test Championship, to seeing our music tour hit the road againafter 18 years, and our first informal 50’s and 60’s matric lunch at the Bill Bowden there’s a real sense of momentum and connection in the air.
packed with sport, reunions, music, and memories — there’s one tradition we’ve taken a fresh look at: the Annual Old Boys’ Dinner. It’s always been a special evening full of laughter, reflection, and that unmistakable Wynberg spirit. But we also know it hasn’t always worked for everyone. So this year, we’re trying something new…
The Annual Dinner
It gives me great pleasure, on behalf of the Wynberg Old Boys' Union, to invite you to this year’s Annual Dinner a proud tradition that has stood for nearly 80 years. As always, this event is about more than a meal. It’s about reconnecting with classmates, honouring our shared history, and celebrating what it means to be a Wynberg Old Boy.
Preserving the Tradition, Evolving the Experience
Our Old Boys community now spans over seven decades from recent leavers to men in their nineties.That diversity is something we’re incredibly proud of, but it also presents a challenge: how do we create a dinner experience that welcomes and includes everyone?
The traditional sit-down dinner remains an important part of our heritage and is cherished by many. But we recognise that cost, formality, and changing social preferences can be a barrier to attendance, especially for younger Old Boys.
Introducing a Thoughtful Compromise
This year, for the first time, we’re introducing a dual-format dinner: The traditional sit-down dinner will take place in the school hall, with all the expected dignity and structure. At the same time, we’ll host a more informal gathering outside in the basketball court parking area, with a beer tent, food trucks, and big screens live-streaming all key proceedings from the hall.
During shared moments of reflection — such as tributes to Old Boys we’ve lost, the Principals' & President's addresses, and the calling of the years all service will pause, ensuring we maintain a unified and respectful atmosphere across both spaces.
You’re free to choose the format that best suits you, regardless of your age, and both offer a place to reconnect, reflect, and enjoy the evening your way.
Why This Matters
We know the value of tradition, but also that traditions must grow to stay alive.This is not about replacing the past but about making space for the future, creating a more inclusive, engaging experience that better reflects the full scope of our community. We’ve seen how intergenerational connection happens more naturally at events like sports derbies, open mic evenings, or social events, and we believe this new format gives us a better chance to build those connections, while still preserving the core elements that make the Old Boys' Dinner so meaningful.
Your Support Matters
We understand that change can be difficult, especially when it touches something so longstanding. But we truly believe this evolution reflects the best of what it means to be a Wynberg Old Boy honouring where we’ve come from, while welcoming who we’ve become, and who we will always remain - brothers in an endless chain!
Ticket sales will close on 25 August 2025 for catering and planning purposes unless we reach capacity before that date.
Read the programme for the names of the attendees, and our valued Old Boy sponsors Cheers, London Old Boys!
Huge thanks to everyone who joined Jan de Waal and Karl Westvig for our first London get-together since 2014!
We missed our special guests, Proteas stars David Bedingham and Kyle Verreynne, who were tied up in a warm-up game against Zimbabwe at Arundel Castle Cricket Ground. But how’s this for Wynberg pride? Two Old Boys at the crease helping clinch the ICC Test Championship title for SA on the back of an incredible team effort, which will live on in our memories and our school records.
Shout-out to former WBHS Vice-Principal Mike Engelbrecht for snapping the evening’s highlights.
Here’s to many more reunions in the UK an beyond!
Check out the photo album on Flickr.
Headmasters Deon Scheepers and Cedric Poleman, and the Wynberg Old Boys' Union welcomed a group of Old Boys and former staff to lunch at the Bill Bowden Pavilion on Friday 30 May - in former Headmaster (and WBHS Head Prefect 1966), Bruce Probyn's (summarised) words:
"Well done to the Union on the initiative of connecting us informally here, these events will only grow over the months in celebrating our Alma Mater!" View the photos
Open Mic with Our Old Boy Varsity Cup Rugby Champs
In Cape Town this July? Please join us for a unique Open Mic as we bring our Wynberg Old Boy UCT Rugby men to the Bill Bowden Pavilion for a unique insight into their Varsity Cup-winning campaign this year.
With Nic Groom, Director of Wynberg Rugby and Ikey's Coach, as MC, there's sure to be some great stories to share, off the record, and in-house only.
No phones to record, just a great evening celebrating Wynberg Rugby, beyond the Hawthornden.
Get tickets online
Wynberg Heritage Week 2025
Some venues and times will be confirmed in the weeks ahead.
Friday 22 August
1975 Class Reunion, Bill Bowden Pavilion
WBHS Hockey vs Rondebosch, Home
Saturday 23 August
WBHS Rugby vs Rondebosch, Home
Monday 25 August
Old Boys' Chess & Debating vs WBHS
Old Boys' Squash vs WBHS
Old Boys' Mountain Biking vs WBHS
Tuesday 26 August
Old Boys' Soccer vs WBHS
Old Boys' Hockey vs WBHS
Old Boys' Cross Country vs WBHS, TBC
Wednesday 27 August
Old Boys' Annual Dinner
Thursday 28 August
WBJS Flag Raising Ceremony, 11h00, Arnold Lorie Hall Nussbaum Concert
Friday 29 August
WBHS Founders' Day Ceremony, 11h00, Clegg Hall
WBHS Hockey vs SACS, Home
Old Boys' Rugby Reunion, Bill Bowden Pavilion
Saturday 30 August
WBHS Rugby vs SACS, Home
Old Boy Making News: Sikhumbuzo Notshe
Fantastic to see Wynberg Rugby Old Boy Sikhumbuzo Notshe (Matric 2012 & SA Schools 2011) back in top form!
Underdogs Montauban Rugby Club stun Pro D2 with shock title win – June 2025
"After a sensational break from Josua Vici, the Montalbanaise engaged in a powerful phase-byphase play that could only end in one way: a try. Former Springboks No.8 Sikhumbuzo Notshe ran with the backline to catch the ball and dive in for his team’s first five-pointer."
Notshe’s professional career has seen him don the jerseys of the Stormers and the Sharks. But a string of frustrating injuries stalled his momentum—until a new chapter began in 2024 when he signed with French Pro D2 club Montauban.
Previously fighting relegation, Montauban brought in fresh talent, found their rhythm, and finished 6th securing a surprise playoff spot. Against all odds, they pulled off a huge upset, defeating Pro D2 heavyweights Grenoble in the final.
This victory propels Montauban into the Top 14 for the first time since 2010 a remarkable return to Europe’s top-tier French rugby and a well-deserved moment in the spotlight for Notshe and his team.
Read the full story
Old Boy Making News: Gareth Ramsay
Engineering graduate of Stellenbosch University, 2015 Deputy Head Prefect, Gareth Ramsay “is leading an ambitious campaign to construct a new sky train in Cape Town.
Earlier this year, the local engineer submitted a proposal for the creation of a new elevated railway that will run through Cape Town’s CBD towards the Atlantic seaboard with the goal of improving accessibility and reducing road congestion.
A key aspect of the proposal is that the infrastructure project will integrate with the famous incomplete Foreshore Freeway Bridge, which the city is currently trying to find a use for."
Read more
