Plaskett's early chess years saw him win the World Under-17 Championship in 1976 and became the first player in the history of British chess to qualify as a grandmaster solely by playing in British tournaments in 1985.
Plaskett is known for his aggressive and imaginative style of play, often fearless in the risks he would take, even on positions that may be objectively worse. He has written books about the game and contributed to different chess-related publications worldwide. Additionally, he has won open tournaments in numerous countries, including the United States, Spain, Greece, and Portugal.
Besides chess, Plaskett has two other significant facets to his life and career. The first one is his involvement with games and television shows. Plaskett won £250,000 as a result of his appearance on the UK-based television game show "Who Wants to be a Millionaire" in 2006, after seven years of unsuccessful attempts to get on the program. Additionally, he played the role of John Lennon in the 2000 movie "In His Life: The John Lennon Story". He played bridge at the London Metropolitan Club, competed in poker tournaments, and was a runner-up in the UK Scrabble Championship in 1981.
The second facet is Plaskett's apparent interest in paranormal phenomena. He chronicled a series of coincidences, which he takes to be significant, in his book "Coincidences" (2010). He reported three instances where he sensed that a person was about to die, and they did. These experiences lead him to call for more scientific research into coincidences. Despite many people's scepticism regarding such phenomena, Plaskett remains publicly committed to his theory.