HEADLEDGE Meaning of HEADLEDGE in English ˈ ̷ ̷ˌ ̷ ̷ noun 1. : either of the athwartship coamings of a hatchway or other deck opening2. : either of the upright end posts of a centerboard box Webster's New International English Dictionary. Новый международный словарь английского языка Webster. 2012