Henry Willoughby may refer to:
- Sir Henry Willoughby (1451-1528)
- Sir Henry Willoughby, 1st Baronet (1579–1649), see Sir Thomas Aston, 1st Baronet
- Henry Willoughby, 4th Baron Willoughby of Parham (c. 1603–1618)
- Henry Willoughby (governor) (1640–1669), governor of Antigua and Barbados
- Henry Willoughby, 16th Baron Willoughby of Parham (d. 1775)
- Henry Willoughby, 5th Baron Middleton (1726–1800)
- Henry Willoughby, 6th Baron Middleton (1761–1835)
- Henry Willoughby (MP) (1780–1849), represented Newark (UK Parliament constituency)
- Sir Henry Willoughby, 3rd Baronet (1796–1865)
- Henry Willoughby, 8th Baron Middleton (1817–1877)
- Henry Willobie, also written 'Willoughby'
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