Born in Canton, North Carolina, Hipps received numerous awards in 1926 while playing baseball at Furman University. Connie Mack of the Philadelphia Athletics signed Hipps to play with a number of  AA ball clubs. By 1929, Hipps was teaching and coaching baseball in Weaverville, North Carolina. Between 1927 and 1934, Hipps played for eighteen different ball clubs.  By 1935 at the age of 30, Bobby Hipps joined the Coolemee Cools but transferred to the Kannapolis Towelers, first as a player then as a manager. He managed the Concord Weavers for a while but ended his career in the Outlaw League, managing the Lenoir Finishers. Hipps served as president of the class "B" Tri- State League, from 1951 to 1955.