Bobby Shaftoe may refer to:
- Bobby Shafto, 18th Century English politician and subject of a famous song.
- Bobby Shafto's Gone to Sea, the song itself.
- Bobby Shaftoe, a lead character in Neal Stephenson's novel Cryptonomicon.
- Sergeant Bob Shaftoe, a 17th century character in Stephenson's The Baroque Cycle, brother of Jack Shaftoe, an ancestor of Bobby Shaftoe.