Ray McHale came through Chesterfield's junior ranks and played on the wing in the '68-9 side that won the Northern Intermediate League Cup. By the time of his first-team debut he was converted to a midfielder and became respected for his persistent, tireless approach, his aggressive but skilful play and for his thunderbolt shot and his success rate at penalties (Ray converted eleven out of twelve in his time at Saltergate.)

In 1974 Ray was transferred to the relative obscurity of The Shay in exchange for Terry Shanahan, after a dispute over loyalty bonuses that embroiled several of Chesterfield's leading players. Shanahan averaged a goal every other game and stands twelfth in the list of all-time Town goalscorers, yet the deal was perceived as a poor one, given the success that Ray achieved at Swindon, and given the money that changed hands as he was subsequently transferred.

A peripatetic career took him to Swindon, Brighton, Barnsley, Sheffield United, Bury, Swansea, Rochdale and Scarborough. Non-league football beckoned and he took his first steps in management after hanging up his boots at Guiseley, guiding that team to success in the FA Vase and Northern Premier League. Scarborough first appointed him to the manager's post in November 1989, ten months after he had joined them as Assistant Manager (he became the fourth ex-Spireite to manage Scarborough since World War Two) and they enjoyed some success under him. He left in April 1993 after a dispute with the Chairman and returned to Guiseley. In December '94 he went back to Seamer Road as Manager but moved aside to the assistant's position in March, 1996. When Mick Wadsworth left Scarborough for Colchester in January 1999, Ray assumed joint caretaker-managership with Kevin Ratcliffe. He continued to serve the Seadogs in a number of roles before leaving to serve Oldham Athletic as Chief Scout in November 2001. This lasted only until the summer of the following year, though, when that club's financial troubles began to bite and Ray was relieved of his duties.

After leaving Oldham Ray became an FA Tutor before moving to Palomares, in Spain, where he coaches young players and plays golf off a very low handicap.

For Chesterfield: 123 + 1 league appearances, 27 goals.