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Plaskett has been recording his own experiences of coincidences since the 1980s. He has said that the coincidences have seemed to proliferate in response to his own study, and have been seemingly interlinked by recurrent themes or motifs, which he felt may be "an indicator of something glimpsed but yet to be clearly seen or understood." He is the author of a semi-autobiographical book, Coincidences.
After appearing four times at the qualifying stage of Who Wants to Be a Millionaire?, Plaskett, who had arrived with fellow grandmaster and friend Stuart Conquest, got into the hot seat on a show broadcast on 21st January 2006. After becoming the seventh and last person to reach £125,000 without using any lifelines, he went on to win £250,000.
He has been public in his defence of contestants Charles Ingram, Diana Ingram, and Tecwen Whittock, who were found guilty of cheating to win the £1 million top prize by means of cough signals. Plaskett told journalist Jon Ronson that the alleged cough signals were simply nervous, responsive coughing caused by unconscious triggers, and that they had also occurred during the legitimate win by Judith Keppel. In 2015, Plaskett and journalist Bob Woffinden collaborated on a book asserting that the Ingrams were innocent. The book, titled Bad Show: The Quiz, The Cough, The Millionaire Major, was published in January 2015. Plaskett's book on the Ingram affair inspired a stage play by James Graham, called Quiz.