Sir Henry Guildford, KG (1489–1532) was an English courtier of the reign of Henry VIII, master of the horse and comptroller of the royal household.
He was the son of Sir Richard Guildford by his second marriage. His mother was Joan, sister of Sir Nicholas Vaux, 1st Baron Vaux of Harrowden.
On the accession of Henry VIII, he was a young man of twenty, and a favourite with the new king. On 18 January 1510 he and his half-brother, Sir Edward, formed two of a company of twelve in a performance described by Hall, got up for the amusement of the queen. Eleven of them impersonated Robin Hood and his men, and with a woman representing Maid Marian surprised the queen in her chamber with their dancing and mummery. Next year, on Twelfth Night, he was the designer of the pageant with which the Christmas revelries concluded: a mountain which moved towards the king and opened, and out of which came morris-dancers.
At the tournament next month, held in honour of the birth of a prince, he signed the articles of challenge on the second day. Immediately afterwards he went with Lord Darcy's expedition to Spain against the Moors, where the English generally met with such a cool reception; but he and Sir Wistan Browne remained a while after their countrymen had returned home, and were dubbed knights by Ferdinand at Burgos on 15 September 1511. Early next year they had both returned, and received the same honour at the hands of their own king at the prorogation of the parliament on 30 March 1512. Hitherto he had been only squire of the body, a position he seems still to have retained along with the honour of knighthood. He was also a ‘spear’ in the king's service, and of as 29 March 1510 he had a grant of the wardship of Anne, daughter and heiress of Sir John Langforde.
In May 1512 he married Margaret, daughter of Sir Thomas Bryan. The king's sister, Mary, at that time called Princess of Castile, made an offering of six shillings and eightpence at his marriage. On 6 June the king granted to him and his wife the manors of Hampton-in-Arden in Warwickshire and Byker, Lincolnshire. On 3 December he was appointed bailiff of Sutton Coldfield in Warwickshire, and keeper of Sutton Park; on the 24th constable and doorward of Leeds Castle, and keeper of the parks of Leeds and Langley in Kent.