Henry Caldwell (–1810) was a Canadian army officer.

Henry Caldwell may also refer to:

Henry Clay Caldwell (1832–1915), United States federal judge and Union Army officer Henry John Caldwell (1801–1858), Quebec politician Henry M. Caldwell, Mayor of Birmingham, Alabama in 1878 Sir Henry Caldwell, 2nd Baronet (died c. 1726), of the Caldwell baronets Sir Henry John Caldwell, 7th Baronet (1801–1858), of the Caldwell baronets

See also John Henry Caldwell, (1826–1902) US Representative from Alabama Harry Handley Caldwell, (1873–1939) America's first submarine captain