Simon Bailey may refer to:
- Simon Bailey (priest) (1955–1995), Anglican priest and writer
- Simon Bailey (archivist), Keeper of the Archives at the University of Oxford in England
- Simon T. Bailey (born 1968), American speaker, author, life coach and entrepreneur
- Simon Bailey (police officer), Chief Constable of the Norfolk Constabulary
- Simon Bailey (runner) (born 1980), English fell runner
- Simon Bailly, English politician
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