Sean Biggerstaff first appeared in the 1996 four-part television miniseries ‘The Crow Road’ directed by Gavin Millar. The following year, he made his big-screen debut in the Alan Rickman-directed drama film ‘The Winter Guest.’ The film received a positive response from critics and grossed over $1.3 million at the box office. In 2001, he portrayed ‘Oliver Wood’ in the fantasy film ‘Harry Potter and the Philosopher's Stone’ directed by Chris Columbus. The film earned praise from critics and was a massive box office success, grossing over $974 million on a budget of $125 million. The following year, Biggerstaff reprised his role as ‘Oliver Wood’ in the fantasy film and the second installment of the Harry Potter film series, ‘Harry Potter and the Chamber of Secrets’ directed by Chris Columbus. The film opened to a positive reception and was a phenomenal commercial success, managing to gross over $879.8 million on a budget of $100 million. He next played the role of ‘Henry, Duke of Glocester’ in the 2003 British television film ‘Charles II: The Power and the Passion’ directed by Joe Wright. The film was released in 4 episodes. Biggerstaff next became a recipient of the BAFTA Scotland for his portrayal of ‘Jeremy Wolfenden’ in the 2007 BBC Four television film ‘Consenting Adults’ directed by Richard Curson Smith.
In 2009, he appeared in the British ITV television program ‘Agatha Christie's Marple’ where he played the role of ‘Bobby Attfield.’ In 2011, he made a cameo appearance as ‘Oliver Wood’ in the fantasy film and the final installment in the Harry Potter film series, ‘Harry Potter and the Deathly Hallows – Part 2’ directed by David Yates. The film received wide acclaim upon release and was a phenomenal commercial success, becoming one of the highest-grossing films of all time. He next played the role of ‘Earl of Bothwell’ in the 2013 Thomas Imbach-directed Swiss period drama film ‘Mary Queen of Scots.’ The film had its premiere at the Locarno Film Festival. In 2016, he starred as ‘Sergeant Donald Odd’ in the British film ‘Whisky Galore!’ directed by Gillies MacKinnon. The film received a mixed response from critics and holds a 42% approval rating on Rotten Tomatoes. In 2019, he joined the cast of the British biographical comedy-drama television series ‘Urban Myths’ as ‘Billy.’ He starred in 2 episodes and remained a part of the show until 2020.