Keay was born in Whiteinch, Scotland and played as a youth for various local sides before starting his professional career at nearby Partick Thistle.

In the spring of 1895, Charles Robson, the newly appointed secretary/manager of Southampton St. Mary's, and Alfred McMinn, one of the club committee, visited the Midlands in search of new players to strengthen the team ready for their second season in the Southern League.

Port Vale and Stoke lodged a complaint with The Football Association about "poaching", and an emergency FA meeting was held at Sheffield, resulting in the Saints being severely censured for negligence.

Southampton exceeded the achievements of the two previous seasons, winning the Southern League title without losing a match, as well as reaching the Second Round Proper of the FA Cup, where they went out to Newton Heath in a replay.

[5] The 1897–98 season followed a similar pattern, with Southampton retaining their league title, and advancing to the semi-final of the FA Cup, losing to Nottingham Forest in a controversial replay.

Joe Turner had moved to Stoke in the summer of 1898 and The "Saints" struggled to find an adequate replacement at outside-right, with neither Jim McKenzie nor George Seeley holding down the position for long.