Harry Stafford was born in Crewe in 1869. He worked as a boiler-maker but also played football for Southport Central on a Saturday afternoon.
In 1892 Stafford signed for Crewe Alexandra and three years later played an important role in Crewe's good FA Cup run. At the end of the 1894-95 season Stafford was offered a job working for the Lancashire and Yorkshire Railway (LYR) on the understanding he would play for Newton Heath, the works team. Stafford was appointed captain and became the dominating force at the club.
Garth Dykes pointed out in The United Alphabet that Stafford was "noted for his snappy dressing, which included a liking for white hats and brilliantly-hued waistcoats."
Newton Heath had serious financial problems. In 1901 the club staged a four-day grand bazaar in St James Hall, Oxford Street, Manchester. The club needed to raise £1,000 in order to avoid bankruptcy. Even though Manchester City even made a donation, by the end of the third day it seemed that the venture would prove unsuccessful.
Harry Stafford had the idea of using his St. Bernard dog, Major, to raise money. He wandered amiably between the stalls with a collection box strapped to his back. It was hoped that the dog would attract donations. On the fourth day of the grand bazaar Major escaped from St. James Hall. He eventually found his way to the home of a rich businessman, John Henry Davies, who owned a successful brewery in Manchester. Davies liked the animal and decided to buy the dog for his daughter. When he traced the dog's owner, Stafford told Davies about the financial position of Newton Heath. The two men became friends and decided to make a takeover bid for the club.
By 1902 Newton Heath was £2,670 in debt and faced a winding-up order. At a shareholders' meeting in the New Islington Hall, Harry Stafford announced that he and four local businessmen, including John Henry Davies, were willing to takeover the club's debts. The Football League approved the plan and Newton Heath now became Manchester United. It was also decided that the club would now play in red shirts and white shorts.
Stafford, along with Davies, became a director of Manchester United and James West was appointed as manager. Davies arranged for J.J. Bentley to be appointed as president of the club. However, at the end of the 1902-03 season West and Stafford were suspended by the Football Association for making illegal payments to players. In his defence, Stafford claimed: "Everything I have done has been in the interests of the club."
With the help of John Henry Davies, Stafford ran an hotel in Wrexham. Later he moved to Canada where he owned a large hotel where the Ottawa and St. Lawrence met. By 1922 the amenities of the hotel included pitches for football, baseball, lacrosse and cricket. There were also tennis courts and a 250 yard track for whippet racing.