James Winchester (1752–1826) was an American Revolutionary War officer and brigadier general during the War of 1812.

James Winchester may also refer to:

• James Winchester (Maryland judge) (1772–1806), Maryland politician and judge
• James R. Winchester (born 1952), Chief Justice of Oklahoma
• Jesse Winchester (1944–2014), stage name of James Ridout Winchester, American musician
• James Winchester (American football) (born 1989), American football player
• James Ridout Winchester (1852–1941), bishop of the Episcopal Diocese of Arkansas

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