Headleigh \he(a)-dlei-gh, head-leigh\ as a boy's name is a variant of Hedley (Old English), and the meaning of Headleigh is "heathered meadow". The baby name Headleigh sounds like Hadleigh and Headley. Other similar baby names are Hagleigh, Hayleigh, Haleigh, Henleigh, Hanleigh, Handleigh, Harleigh, Hawleigh, Radleigh, Redleigh and Wadleigh.