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.
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".
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.
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.
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".
[citation needed] After having had an administrative position with a Dutch side, in January 1959 he became successor of Stan Rickaby at Southern League club Poole Town.
[9] Between September 1960 and January 1961, when he unexpectedly resigned for family reasons, he returned to England to get married, he was manager of the Dutch second division side Heracles Almelo.