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Known challenges Edit
When they were captured by the Master, Jo Grant and the Third Doctor played chess against each other. Jo won and took all the Doctor's remaining pieces. The Doctor complained that the trouble with this game was that it was too simple. Furthermore he mentioned that he was more used to playing three dimensional chess. (TV: The Mind of Evil)
K9 Mark I played chess with the Fourth Doctor in the TARDIS. Leela had to move K9's pieces for him. The Doctor declared that even one-dimensional chess showed the failings of the mechanical brain, shortly before K9 put him in check. (TV: The Sun Makers) A match with K9 Mark II saw the Doctor moving K9's pieces. (TV: The Androids of Tara)
In 1889, in the House of the Dragon, the Fourth Doctor and Magnus Greel played a few moves of chess with the Doctor checkmating his opponent, who scattered the pieces in anger. (TV: The Talons of Weng-Chiang)
Chess was particularly favoured by the Seventh Doctor when battling certain enemies (in particular Fenric). He was accused by Ace and Bernice Summerfield of playing with their lives "as though you would a game of chess". (TV: The Curse of Fenric) [additional sources needed] While battling Lady Peinforte, de Flores and Cybermen, the Seventh Doctor and Ace travelled to 1638, where the Doctor played chess against an unknown opponent (thought to be Fenric). (TV: Silver Nemesis) The Seventh Doctor played chess against Anthony Rupert Hemmings while the latter posed as his friend George. (PROSE: Timewyrm: Revelation) The Seventh Doctor and his companions Ace, Hex, Lysandra, and Sally were transported by Fenric to a pocket universe resembling a chessboard. (AUDIO: Gods and Monsters)
Darius Pike (with the help of K9 Mark 2) played chess against Starkey (aided by Jorjie Turner). Starkey beat him. The particular chessboard on which they were playing had animals as the chess pieces. (TV: The Fall of the House of Gryffen) Starkey later lost to K9. (TV: The Cambridge Spy)
The Eleventh Doctor once played Bobby Fischer and refused to do so again because it went "very wrong." He also had a habit of playing himself and was disappointed because every time he played chess against himself he lost. (PROSE: Dark Horizons)
Humphrey, a fictional character created by Annette Billingsley, was taught chess by his grandfather and used his knowledge to beat a minor villain in one of Billingsley's The Troubleseekers novels. When a Ch'otterai brought The Troubleseekers fictional world to life, the Tenth Doctor encountered the robber and agreed to his challenge of a game of chess. However, the Doctor said it was inevitable that he would win because he had never lost a game of chess except to a metal dog which did not count, so he refused to play the game and claimed victory anyway. (PROSE: The Mystery of the Haunted Cottage)