Robert Bailey may refer to:

• Rob Bailey (cricketer) (born 1963), English cricketer and umpire
• Rob Bailey (director), English television director
• Rob Bailey (musician) (born 1953), Australian bass guitarist
• Robert Bailey (American football) (born 1968), American football cornerback
• Robert Bailey (epidemiologist), American epidemiologist
• Robert Bailey (geographer) (born 1939), American geographer
• Robert Bailey Jr. (born 1990), American actor
• Robert D. Bailey Jr. (1912–1994), West Virginia secretary of state
• Robert D. Bailey Sr. (1883–1963), American judge involved in the Matewan Massacre trials
• Robert E. Bailey, U.S. Air Force general
• Robert L. Bailey (1922–2018), politician in Oklahoma
• Robert B. Bailey (1892–1957), lieutenant governor of Arkansas

• Robert D. Bailey (disambiguation)
• Robert Baillie (disambiguation)
• Robert Bayley (died 1859), English independent minister
• Bob Bailey (disambiguation)