An alumnus of Haberdashers' Aske's School, Sutcliffe started his career with a novel about school life entitled New Boy (1996), which was followed by his best-known work so far, Are You Experienced? (1997), a pre-university gap year novel, in which a group of young Brits travel to India without really knowing what to expect or what to do there. The Love Hexagon (2000) is about six young Londoners who have difficulty committing themselves to a relationship. Bad Influence (2004), is about Olly, a 10-year-old growing up in a North London suburb with his family, and the plot centres on the complex knot of his childhood friendships. Sutcliffe's 2008 book Whatever Makes You Happy (2008) is about interfering mothers and men who refuse to grow up. His first young adult novel, "The Wall" (2013), tells of a boy in Israel's occupied territories whose discovery of a tunnel underneath the barrier wall sets off a spiraling chain of events after he goes under and is saved from his attackers by a girl on the other side.
Sutcliffe's novels could be categorised as humorous. New Boy has much authentic material in it that refers to actual incidents from his life at Haberdashers', although it would be going too far to call it "autobiographical".
In 2009, he donated the short story Sandcastles: A Negotiation to Oxfam's 'Ox-Tales' project, four collections of UK stories written by 38 authors. Sutcliffe's story was published in the 'Fire' collection.