Mr. Dippenaar joined the Hilton College staff in 2004 as choirmaster, bringing with him hisl experience from the Drakensberg Boys Choir School and a Master’s Degree in choral conducting. He changed the then Hilton College Chapel Choir to a Concert Choir, with attendant changes in repertoire.

The main body of choristers is divided into voice groups for rehearsal purposes and each group rehearses twice a week for an hour. This allows the choirmaster to work with smaller groups and encourages choristers to know their parts well as they sing in a more exposed environment.

Touring is an integral part of any choir's development, and the Hilton College Tour Choir is auditioned from the main body of choristers, and usually consists of about 40 members. A tour is undertaken each year. In 2005 the choir traveled to the Western Cape and performed in Langebaan, Saldhana and Cape Town. In 2006 they visited Mpumalanga and performed in Sandton, White River, and Skukuza. In 2007 the choir toured the Southern Cape, and performed in George, Mosselbay and Plettenberg Bay. School demonstrations form an integral part of such a tour, and we encourage pupils from these schools, especially boys, to become involved in music and the arts.

The Hilton College International Choir is an even more select group of choristers that form a chamber choir of about 45 members. In 2006 they took part in the Michaelhouse Provincial Choir Competition where they won first prize in the Chamber Choir section. The whole choir was awarded Half Colours for this achievement.

In 2008 the choir, comprising 45 members, participated in the World Choir Games, also known as the Choir Olympics. This prestigious competition took place in Graz in Austria over the June/July school holidays.  The choir also visited Turkey en route to Austria.