Bobb played his first tournament at the 1921 All India Championships where he reached the final and secured his first singles title.

[3] In major tournaments he took part one time at the 1928 Wimbledon Championships where he reached the second round before losing to the American player Wilbur Coen in straight sets.

That year he also played in Italy where he reached the final of the TC Juventus Torino Championship in Turin on clay, before losing to Mohammed Sleem in straight sets.

His other career singles highlights included winning multiple titles at the Western India Championships three times (1934, 1939–1940), the Bombay Presidency Hard Court Championships four times (1934-1935, 1938, 1940).

During World War II, Bobb joined the Royal Indian Navy Volunteer Reserve and served as a Paymaster Lieutenant in May 1939.