Having been an apprentice at Charlton Athletic, Kamara signed professional forms for Watford in June 2006 after a trial spell.
Kamara's 2006-2007 pre-season was disrupted with a knee injury which it was initially feared would keep him out for the entire season. However the injury was proved to be less serious than originally thought, only keeping him out of action for around a month.
On the 1 May 2008, Sheku Kamara was sentanced to 8 years in jail for his involvment in an armed robbery. He was arrested as part of a gang of criminals who would confront civilians with a gun and ask for their possessions, including mobile phones, wallets and pin numbers.
In passing sentence, the judge described the men's actions as well-planned and intentional banditry of the worst order. He commended the arresting officers for their bravery and the investigating team for the professionalism of their work.
The three men were identified and arrested, in late November 2007, after local police increased patrols and CCTV was monitored in response to a spate of similar robberies in the area during November 2007.
The victims of these robberies were threatened at gunpoint and had credit cards, cash and other valuables stolen. They would then be forced to provide their PIN and one of the robbers would go to a nearby cash machine and withdraw money.
Kamara was charged with five counts of robbery and five counts of possession of a firearm with intent to cause fear of violence. Two firearms believed to have been used in the robberies were also recovered during the investigation, a gas-powered airsoft gun, modelled on a Smith & Wesson pistol and a .177 calibre air pistol.