Chess is a hugely popular past-time at Wynberg, with many informal challenges taking place in the Library every break time and afternoon.

Our teams are highly competitive and enthusiastic and have succeeded in encouraging a wider following of chess within the school. Coaching takes place every Wednesday afternoon in the Library, and all boys are welcome. Our Chess Ladder (situated in the A corridor), has 32 names on it and boys are encouraged to challenge each other to move up the ladder. The top 12 boys make up the three match teams every Friday.

Our best showing at the Grey College Chess Tournament was in 2010 when we won the Bronze medal. In 2011 we were placed 11th – the best of the Western Cape schools. In 2009, Wynberg created the Jamie Tindill Memorial Chess Tournament in honour of Jamie who died tragically in 2008. He was an outstanding chess player and Service Prefect at this school. The Tournament involves 8 local schools, the current holders of the trophy being Settlers High School. Wynberg has won the Rondebosch Blitz Doubles Tournament on two occasions in the last seven years, the last time being in 2010.

Western Province Representatives:
Our best achievements in the past were top 20 placings for Stephen Bell (2007) and Jamie Tindill (2008). Currently, Guy Green is our only provincial representative, having made the WP U16 team last year and the WP U20 squad for 2011.

We have three teams playing in the A B and C leagues at present. Each team consists of four players. The League is a tough one with automatic relegation for the bottom team and automatic promotion for the top team at the end of every term. In 2009 and 2010 we had two teams in the A league.

Annual Tournaments:
• Grey College Chess Tournament in Bloemfontein
• The Jamie Tindill Memorial Tournament
• Blitz Doubles Tournament, hosted by Rondebosch Boys’ High
• Interhouse knock-out tournament.