Keeping was born in Milford on Sea where he was spotted playing for his home-town club, Milford on Sea F.C., and was signed by Southampton, then still in the Southern League, in the summer of 1919 for a bargain fee of £25. Still only 16, Keeping was registered as an amateur but paid 10 shillings a week for travelling expenses. He signed as a professional in December 1920 but only made his first-team debut on 25 October 1924, in a Football League Division 2 match at Hull City as a replacement for the long-serving Fred Titmuss who was injured. In his first season he made only seven league appearances. In the following season, he again started as an understudy to Titmuss but in October he took over at left-back and retained his position, with Titmuss leaving the club in February 1926. He soon blossomed into an outstanding left-back who "oozed class and being fleet of foot could turn on the run to sweep the ball straight up the touchline to the waiting winger". He was selected for an international trial in February 1926 and joined an F.A. party on a tour of Canada in the summer. He continued to display his skills in the Second Division and was an ever-present for the Saints in 1926–27 both in the league and in their run to the F.A. Cup semifinal at Stamford Bridge on 26 March 1927, which Southampton lost 1–2 to Arsenal. During this season manager Arthur Chadwick soon settled on his favoured line-up with eleven players featuring in at least 35 of the 42 league games; Keeping lined up in defence with Ted Hough behind the three centre-backs – Bert Shelley, George Harkus and Stan Woodhouse. He missed the start of the 1927–28 season due to illness, but was otherwise a regular starter throughout the next four seasons as Saints regularly finished in mid-table. He played for the "Professionals" in the 1929 FA Charity Shield. He made a good start to the 1931–32 season and won his only representative honours when he played for the Football League against the Irish League in September 1931. He was then struck down with appendicitis in January and was out for the rest of the season. In February 1933 Southampton needed to raise cash and they sold Keeping and Johnny Arnold to Fulham for a combined fee of £5,000, with Arthur Tilford temporarily joining the Saints. Jimmy McIntyre, the former Saints manager now in charge at Fulham boasted that this was "the best deal I ever brought off". In his playing career at The Dell, Keeping made a total of 281 appearances for the Saints, scoring twelve goals. In Holley and Chalk's "Alphabet of the Saints", Keeping is described as "a debonair man, contemporaries recall him as being equally stylish off the pitch and, much to the amusement of his team-mates, he would take hours over his appearance".
Fulham
Keeping joined Fulham in February 1933 and served them well until the outbreak of World War II in 1939. He continued to turn out occasionally for Fulham until 1941 when he returned to Milford to join the family motor business.
