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Simon Cooper was the runner-up of Series 41. He was a Conference Centre Manager from St. Neot's, Cambridgeshire.
He first appeared on 14 September 1999, beating Steve Clark 47 – 40. He won a further seven games to become an octochamp with an impressive points total of 482, however in that series it was only good enough for #3 seed. Simon beat Margaret Foster and Gary Woodward on his way to the final against Scott Mearns. Unfortunately for Simon, Scott's blistering form that he had displayed throughout the series continued unabated. Simon lost the game 81 – 73 and had to settle for the runner-up's prize. Simon returned the following week for Championship of Champions X, but lost in the first round to Terence English.
|#||Date||Type||Contestant 1||Score||Contestant 2||Presenters||Guest||Lex||Max|
|2599||14/09/1999||P||Steve Clark||40 – 47||Simon Cooper||Richard Whiteley||Carol Vorderman||Rick Wakeman||Mark Nyman||69|
|2600||15/09/1999||P||Simon Cooper||51 – 28||Lisa Eyers||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||84|
|2601||16/09/1999||P||Simon Cooper||69 – 55||Niall Spooner-Harvey||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||85|
|2602||17/09/1999||P||Simon Cooper||72 – 14||Raymond Ogilvie||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||73|
|2603||20/09/1999||P||Simon Cooper||65 – 43||Ola Odutola||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||73|
|2604||21/09/1999||P||Simon Cooper||61 – 37||Lynne Savin-Smith||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||73|
|2605||22/09/1999||P||Simon Cooper||55 – 31||John Grisdale||Richard Whiteley||Carol Vorderman||Tom O'Connor||Damian Eadie||74|
|2606||23/09/1999||P||Simon Cooper||62 – 51||Andrew Fenton||Richard Whiteley||Carol Vorderman||Angela Rippon||Damian Eadie||84|
|2669||21/12/1999||QF||Simon Cooper||57 – 40||Margaret Foster||Richard Whiteley||Carol Vorderman||Carol Barnes||Damian Eadie||83|
|2672||24/12/1999||SF||Gary Woodward||41 – 64||Simon Cooper||Richard Whiteley||Carol Vorderman||Rick Wakeman||Catherine Clarke||84|
|2673||25/12/1999||GF||Scott Mearns||81 – 73||Simon Cooper||Richard Whiteley||Carol Vorderman||Rick Wakeman||Catherine Clarke||116|
|2674||27/12/1999||CQF||Simon Cooper||39 – 58||Terence English||Richard Whiteley||Carol Vorderman||Nigel Rees||Mark Nyman||83|