Roberts was born in Liverpool. As a 16-year-old he spent a season with Everton, and then played for Harrowby. He joined Chesterfield in September 1939, just before the Football League was suspended for the duration of the Second World War. During the war, Roberts served with No. 2 Commando. He was wounded in the legs and captured during Operation Chariot, the raid on the French port of Saint-Nazaire in 1942, and owed the possibility of a football career to the repair work carried out by a German surgeon. Roberts spent years in a prisoner-of-war camp in Bremen. On his return, he lodged with Chesterfield coach and former England international Joe Spence, whose individual work with Roberts played a major role in his recovery.