'bailieship' originates from Scots, specifically the word 'bailie' (from Old French 'baillie'), combined with the suffix '-ship' (from Old English 'scipe' meaning 'state, condition, or office').

'bailie' changed from Old French 'baillie' (meaning 'administration, charge' or an official in charge) and, with the Old English/early Germanic suffix '-ship', formed the Scots/English compound 'bailieship' referring to the office or jurisdiction of a bailie.

Initially it meant 'the office, jurisdiction, or charge of a bailie', and this core meaning has remained largely unchanged in modern usage.