Hugh was the son of Edmund Willoughby and Isabel Annesley, and great-grandson of Sir Richard Willoughby . By his second marriage to Margaret Freville he acquired the valuable manor of Middleton and other estates in Warwickshire, making him one of the wealthiest members of the Midlands gentry. Middleton was to become one of the family's principal residences. Hugh was knighted at the coronation of Henry VI in 1429 and held local offices appropriate to his status.
Sir Hugh and his first wife were buried in the church at Willoughby-in-the-Wolds under a tomb chest with elegant alabaster effigies.
Sir Hugh married 1stly, c.1395, Isabel Foljambe (d 1417), and had:
Hugh married 2ndly, by 1419, Margaret Freville (d 1493, m 2ndly Richard Bingham, Justice of the King's Bench (d 1476)), and had:
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