Connery was born and raised in London. He is the son of Scottish actor Sean Connery (1930-) and his first wife, the Australian Actress Diane Cilento (1933–2011). He attended Millfield School, a co-educational independent school in the village of Street, in Somerset, England, and later the independent Gordonstoun School in Moray, Scotland. He was later accepted into the Bristol Old Vic Theatre School.
Connery performed many roles in theatre and subsequently had parts in several B-films. His film début was in The Lords of Discipline (1983). He appeared in the Doctor Who serial Vengeance on Varos in 1985; he also portrayed Robin Hood in the final season of the television series Robin of Sherwood in 1986.
He later portrayed James Bond creator Ian Fleming in the 1990 television drama Spymaker: The Secret Life of Ian Fleming. In 1997, he appeared in a fantasy film (originally intended as a pilot episode for a longer series); playing the title role of Merlin in Merlin: The Quest Begins, directed by David Winning. He appeared in Faithful Dealing (2001) in London, an English Restoration Whodunit, produced by Dominic Madden. In 2003, he toured with a stage production of The Blue Room. In 2004, he was a main character in the children's show Shoebox Zoo and returned in the second series in September 2005.
Connery had starring roles in several horror films, including Lightspeed (2006), Night Skies (2007), and Brotherhood of Blood (2007).
In 2008, he made his directorial début with the film Pandemic and in 2009 directed The Devil's Tomb. Connery directed the 2011 "After Dark Originals" film 51, and The Philly Kid (2012) for the "After Dark Action" series.
In 2014, he took part in BBC One's Celebrity MasterChef.