Old Boys’ Union
Wynberg Boys’ High and Junior School maintain a robust connection with its alumni through the Old Boys’ Union. The organisation plays a pivotal role in fostering a sense of community and belonging among the school’s graduates, while providing a support base of brothers in an endless chain for the two schools.

WBHS Music Staff on Stage with Andrea Bocelli
Wednesday 16 April 25: Andrea Bocelli’s 30 Year Anniversary Tour electrified Cape Town, packing in music-lovers at the DHL Stadium in Green Point for an unforgettable evening with ‘the world’s […]
Wynberg Golf Season Tees Off with Encouraging Performances
Monday 14 April 25: The golf season is officially underway, with Wynberg’s 1st and 2nd teams in action on their home course at Westlake. The 1st team took on Durbanville […]
U14A & U15A Rugby at the Kwaggas Festival
Thursday 10 April 25: Wynberg has been attending the Kwaggas Rugby Week for about 10 years. It is hosted by Outeniqua High School in George and is attended by top rugby […]
Take-Home Hot Meal Menu, Monday 14 – Thursday 17 April 25
Thursday 10 April 25: The weekly take-home hot meal opportunity by Feedem, our WBHS caterers of choice. Based on a set menu, daily meals for the school week ahead may […]
Take-Home Hot Meal Menu, Tuesday 8 – Friday 11 April 25
Thursday 3 April 25: The weekly take-home hot meal opportunity by Feedem, our WBHS caterers of choice. Based on a set menu, daily meals for the school week ahead may […]
Reflections on the Standard Bank Wynberg Rugby Festival 2025
Thursday 20 – Sunday 23 March 25: A full weekend of 91 fixtures across u14, U15, U16, and U19 age groups at the Standard Bank Wynberg Rugby Festival – thanks […]
The Legacy Fund, Investing in Wynberg’s Future
View photos of the Legacy Fund function at the Oude Wijnberg Museum Thursday 21 November 24: Former WBHS Headmaster and Director of the Old Boys’ Legacy Fund, Jan de Waal, […]
Littlewood House: Prize Giving & Christmas Dinner
View photos of the evening on Flickr Tuesday 24 November 24: The annual Littlewood House year-end – Christmas Dinner & Prize Giving, and a final farewell to the Matric boarders […]
Matric Valedictory & Prize Giving 2024
Wednesday 9 October 24, Matric Prize Giving at the Valedictory Service: Congratulations to all the award winners across the four pillars of Wynberg – Academics, Service, Culture, and Sport. Friedlander […]
In Memoriam: Gabriel Hawkins, Matric 2023
It is with great sorrow that we announce the passing of Wynberg Old Boy, Gabriel Hawkins Matric 2023, who sadly lost the fight to leukaemia on Friday 30 August 2024. […]
Wynberg Heritage Week: Monday 12 – Saturday 17 August 24
Monday 12 – Saturday 17 August 24: Wynberg Boys’ High and Junior Schools, our Wynberg Old Boys’ Union, and our broad community proudly join together in the annual celebration of […]
Beyond our Wynberg Classrooms: Graduate Old Boys on the Move
Wednesday 14 February 24: As we recognise and celebrate the academic achievements of our students during 2023 at Prize Giving, we take a look at a few of our academic […]
Founders’ Day, Friday 25 August 2023
View the Founders’ Day photos Friday 25 August 23: “One of the key elements of Founders’ Day is the pause midway through the proceedings. The first half of the ceremony […]
An Invitation to Wynberg Conversations: Schoolboy Rugby, Wednesday 8 June 2022
Wednesday 8 June 2022: WBHS is pleased to announce the first in a new series of in-person meetings between staff, guests, families, and Old Boys – Wynberg Conversations. The inaugural […]
Together Into 2022, Mr Deon Scheepers’ Message
Friday 31 December 2021, Kaplan House, Wynberg Boys’ High School: Dear WBHS Community I trust that you have been able to spend some quality time with your family and friends […]
Staff Sing Farewell to Jan de Waal ‘Ons Man van Staal’
Wednesday 8 December 2021: The WBHS Staff sang farewell to Mr Jan de Waal with many a tear in the eye. A wonderful al fresco breakfast in front of the […]
Jan de Waal’s Last Assembly as Headmaster: Farewell to the Boys
Tuesday 7 December 2021: The end of the school year and the closing days of our 180th founding celebrations, and our 14th Headmaster, Mr Jan de Waal, delivers his final […]
Remembrance Day 2021: “… And though I never knew you, You are my brothers still.”
Thursday 11 November 2021: As countries across the globe observe Remembrance Day, we pause to consider its relevance here at Wynberg, a South African school that lost no fewer than 43 […]
Sporting Success! At Home and on the Road, October 24
The weekend of 10 – 13 October saw Wynberg host our annual U16 & U19 Basketball Tournament, our 1st XI T20 side head to Twshane to compete in the Westvaal […]
Wynberg Winter Sports Festival 2019
20 – 25 March 2019: Proudly sponsored by Standard Bank, the Wynberg Winter Sports Festival 2019 caters for a cocktail of sports – Rugby, Soccer, and Squash matches will see […]
Wynberg Grey Weekend 2018
Wynberg Boys’ High School Fixtures Times & venues, if not listed, can be found under ‘Details’ Wynberg Boys’ Junior School Fixtures Times & venues, if not listed, can be found […]
Wynberg Sportsmanship: Our Commitment to Positivism in Support
Thursday 26 April 2018: As teaching professionals, and as parents, we are role models to hundreds of boys. Boys observe our behaviour, take it on board and assimilate it, then […]
U14A & U15A Rugby at the Kwaggas Festival
Thursday 10 April 25: Wynberg has been attending the Kwaggas Rugby Week for about 10 years. It is hosted by Outeniqua High School in George and is attended by top rugby […]
Reflections on the Standard Bank Wynberg Rugby Festival 2025
Thursday 20 – Sunday 23 March 25: A full weekend of 91 fixtures across u14, U15, U16, and U19 age groups at the Standard Bank Wynberg Rugby Festival – thanks […]
Standard Bank Wynberg Rugby Festival 2025
Thursday 20 – Sunday 23 March 2025: Please join us as we welcome more than 2200 players to the Wynberg Boys’ High School fields for 4 days of quality rugby […]
Press Report: 1st XV vs Bishops, 27 April 24
View photos of WBHS 1st XV vs Bishops: Album 1 || Album 2 || Album 3 Monday 29 April 24: The report on WBHS 1st XV vs Bishops, as published […]
Press Report: 1st XV vs Paarl Boys’ High, 13 April 2024
View photos of WBHS 1st XV 30 – 27 win vs Paarl Boys’ High on Saturday 13 April 2024 Monday 15 April 24: The report on WBHS 1st XV vs […]
Wynberg on Tour: Kwagga Rugby Day
On Thursday 7 March, the U16, U15, U14 A and B teams departed for George to participate in the Kwaggas Rugby Day on Saturday 9 March. Friday was used, firstly, […]
While alumni of the Wynberg Boys’ Schools have played a big part in the life of the schools since the early 19th century, the Wynberg Old Boys’ Union (WOBU) was formally constituted in 1929. The Union aims to maintain the relationships and bonds formed at school by offering various activities and events. The Union also raises funds for various school initiatives like scholarships and grants. Old Boys support the school by helping in various activities, such as sports coaching, tutoring, mentoring, and providing services and skills as needed by the Wynberg Schools.
Annual Dinners and Class Reunions: WOBU hosts an annual Cape Town dinner for its members during Wynberg Heritage Week in August and a gathering in Gauteng during October. Both these events are supported by the annual Matric reunions of Old Wynbergians, and are mirrored by groups of Old Boys who gather across the globe. All these are opportunities for alumni to come together, celebrate their schools, share experiences, and celebrate their collective history and achievements.
Sports and Events: WOBU is actively involved in supporting sporting and cultural events, reflecting the ongoing passion and dedication of its members to the school’s athletic endeavors. Among the highlights are the annual summer and winter sports matches against the High School teams, and the more cerebral debating and chess contests held during Heritage Week.
Lifelong Connections: At the core of the WOBU is networking and business support for its members, assisting them to maintain lifelong connections with their alma mater and fellow old boys, and fostering a keen sense of community.


Membership of the Wynberg Old Boys’ Union is open to anyone who attended Wynberg Boys’ High and/or Junior Schools at any stage during their school careers.
Staff at the schools are honorary members for their tenure, and an Associate Membership category is available to parents whose sons have completed their schooling at Wynberg.
Contact secretary@wobu.org.za for more information.
A business directory for Old Boys is being developed to include paid and unpaid listings across classified adverts, jobs sought/offered, business and professional services, NPOs, and NGOs.
Helping us to help each other.


The Wynberg Legacy Fund, led by Jan de Waal and Karl Westvig, with Jacques Kallis as the patron, is an Old Boys’ initiative to ensure the viability of the school into the future.
Phase one of The Legacy Fund aims to secure R100 million in pledges by 2027, building an endowment fund that generates significant interest. These gains will be used to provide financial assistance to students who would not ordinarily be able to afford to attend Wynberg, and to assist the school with capital infrastructure projects.