Sir Robert Cary (died c. 1431) of Cockington, Devon, was twelve times Member of Parliament for Devon, in 1407, 1410, 1411, May 1413, April 1414, Mar. 1416, 1417, 1419, May 1421, 1422, 1425 and 1426. Much of his later life was devoted to regaining the many estates and other landholdings forfeited to the crown following his father's attainder in 1388. He was an esquire in the households of King Richard II (1377–1399) and of the latter's half-brother John Holland, 1st Duke of Exeter (c. 1352 – 1400).
He was the eldest son and heir of Sir John Cary (died 1395), Chief Baron of the Exchequer and twice Member of Parliament for Devon by his wife Margaret Holleway, daughter and heiress of Robert Holleway, of Holleway in the parish of North Lew, Devon. Due to his support for King Richard II against Henry Bolingbroke, in 1388 Sir John Cary was attainted by the Merciless Parliament, which resulted in his banishment to Ireland and the confiscation of his lands.
Like his father he was a supporter of King Richard II (1377–1399), during the period of that king's reign when he was challenged by Henry Bolingbroke (later King Henry IV (1399–1413)). In 1391 he became an esquire in the household of King Richard II and in 1392 was also an esquire in the household of Richard's half-brother John Holland, 1st Duke of Exeter, 1st Earl of Huntingdon (c. 1352 – 1400). These connections helped to mitigate the effects of his father's attainder, and he received several grants of land from about 1392. The Parliament of 1398 annulled the Acts of the Merciless Parliament of 1388, and thus Robert Cary recovered some of his father's forfeited estates.