In 1975, his parents decided to immigrate to the United Kingdom, due to the turmoils in Africa. It was there that Simon completed his schooling and was chosen to swim in the British International squad. He competed in Olympic trials and qualified for the 1984 Summer Olympics in Los Angeles. He was offered scholarships to the University of Houston and Southern Methodist University in Texas, where he trained with the United States swimming team, the Mustangs. This would have culminated in him competing in the 1984 Olympic Games. However, after three years of intense training, he decided to quit and return to South Africa, due to his concerns that he was missing out on his social life.
Back in South Africa, Simon entered the air force where he continued his swimming and achieved the highest athletic award given in the air force, the Victor Ludorum.
On his return to South Africa, Simon pursued his stage career as an actor. Whilst studying drama, Simon secured himself a modeling agent and enjoyed success in ramp, print and television commercials. Simon received recognition as a model in South Africa and was asked to enter the Mr. South Africa talent and action man competition. On winning this competition in 1992, Simon was offered an audition on a successful television series, Egoli – Place of Gold. After guest starring on the show for three months, he accepted a permanent contract for a lead role in the show, which he continued for six years.
In 1997, he married his girlfriend Colette in a game lodge in South Africa. After being personally affected by the high levels of crime in Johannesburg, he decided to immigrate to the USA, hoping for a better quality of life. This also gave him the opportunity to further his acting career.
Arriving in 2000 in Los Angeles, Simon secured an agent, and landed a guest star role with Don Johnson on the hit TV series, Nash Bridges. A short time after that, he acquired the guest star role of Ba'al on Stargate SG-1. Cliff's combination of charming bad guy charisma and wicked sense of humor made him a viewer favorite antagonist, keeping his character recurring for five seasons. In 2007, Simon was brought back to play Ba'al in the Stargate movie Stargate: Continuum.
1. Stargate: Continuum (2008) (V) .... Ba'al
2. Stargate SG-1 .... Ba'al (15 episodes, 2001-2007)
3. Nash Bridges .... Dirk van der Goes (1 episode, 2000)
4. Operation Delta Force 5: Random Fire (2000) .... Austin
5. Egoli: Place of Gold (1991) TV series .... Gregory (Mitch) Mitchel (unknown episodes, 1992-1999)