Harold Riley was born in Salford in 1934. As a child he developed a passion for both football and art, but although he had played in the Manchester United junior team as a youth he realised he would never be able to compete at the very highest level and so he went on from his local grammar school in Salford to pursue an artistic career at the Slade in London. He was awarded further scholarships which enabled him to live and paint in Florence and Spain followed by two years National Service in the army. In his mid-twenties, he decided to return to Salford where he started to record the industrial suburbs and pursue the life of an international portraitist.
Riley's interest in football resulted in a spate of portraits of some of football's greatest figures including George Best, Dennis Law and Bobby Charlton. He was given permission to sit on the touchline at important Old Trafford games and from there he made quick sketches or took photographs to use for the painting of football scenes in his studio.