A pupil's high school career at Wynberg starts off with the Grade 8 Blazer Ceremony.  After his first week where the New Boy is told the history of the school, its expectations and its traditions, his parents are invited to a ceremony to witness the formal handing over of his school blazer.  This is done from the stage by his Matric Buddy who also hands over a Certificate welcoming the latest 'brother in the endless chain'.  This certificate exhorts the new Wynbergian to continue the traditions of Good Manners, Pride in Uniform, the School Motto, total involvement in school activities, support of his fellows etc.  As he shakes the hand of the new Wynbergian, the Matric Buddy demands that he must now "Wear his Blazer with Pride'!

 

This ceremony is mirrored 5 years later when a Matric reaches the landmark of the Valedictory Service.  As he prepares to go out into the world, he is welcomed into the brotherhood of the Old Boys' Union.  The Matric and his parents are called up on stage and the Chairman of the Old Boys' Union presents the father of the Matric with his Old Boys' tie which in turn is presented to the Matric.

 

The Prefects' Ceremony takes place annually in October where the outgoing prefects hand over his badge of office to the incoming Prefect.  This ceremony is the culmination of a term of manifestos and meetings where the school has an opportunity to size up all the potential candidates and cast their votes.  In front of their parents and the school, the incoming prefects all sign the following declaration:  "Proudly, yet humbly, and deeply mindful of the honour bestowed upon me, I.... do solemnly swear to uphold the traditions of Wynberg Boys' High School...'