A retired teacher from Scotland, Kennedy first appeared in 2000 where he blundered on a crucial conundrum and lost by 18 points. He returned 17 years later in another close game. He got a crucial conundrum wrong again, but this time wasn’t costly as he was 7 ahead and Alex Smith comically drew a blank. Kennedy followed with his only century of his run and scored no lower than 83 in his remaining six wins, including a 1-point win over Rania Abdul-Wahab.
As a result of his octochampdom, Kennedy returned for the series finals in December, but in a long and strong series, his total of 736 points was only enough to make him the #7 seed. Despite this, he ran #2-ranked Apterite Bradley Horrocks very close in his quarter-final match, leading him by four points going into the crucial conundrum. However, Horrocks came through with a solution to GYRATIONS, and the game's result would ultimately remain true to the seed table.
Two of Kennedy's cousins have subsequently appeared on the show since his appearance – Jane Burns in Series 79, and Burns' sister Monica Quadri, who appeared in Series 80. Less than 3 and a half years after his last appearance, he was the audience member that solved the conundrum on 2 April 2020.
|#||Date||Type||Contestant 1||Score||Contestant 2||Presenters||Guest||Lex||Max|
|2843||20/09/2000||P||Iain Macdonald||58 - 40||James Kennedy||Richard Whiteley||Carol Vorderman||Geoffrey Durham||Damian Eadie||74|
|6690||18/10/2017||P||Alex Smith||73 - 80||James Kennedy||Nick Hewer||Rachel Riley||Adrian Chiles||Susie Dent||132|
|6691||19/10/2017||P||James Kennedy||105 - 39||Krishna Shukla||Nick Hewer||Rachel Riley||Adrian Chiles||Susie Dent||136|
|6692||20/10/2017||P||James Kennedy||88 - 41||Dylan Henderson||Nick Hewer||Rachel Riley||Adrian Chiles||Susie Dent||137|
|6693||23/10/2017||P||James Kennedy||83 - 82||Rania Abdul-Wahab||Nick Hewer||Rachel Riley||Adrian Chiles||Susie Dent||135|
|6694||24/10/2017||P||James Kennedy||99 - 46||Ian Currie||Nick Hewer||Rachel Riley||Adrian Chiles||Susie Dent||132|
|6695||25/10/2017||P||James Kennedy||95 - 80||John Oxley||Nick Hewer||Rachel Riley||John Challis||Susie Dent||146|
|6696||26/10/2017||P||James Kennedy||94 - 61||Mary Anderson||Nick Hewer||Rachel Riley||John Challis||Susie Dent||125|
|6697||27/10/2017||P||James Kennedy||92 - 52||Charlie Turner||Nick Hewer||Rachel Riley||John Challis||Susie Dent||113|
|6731||15/12/2017||QF||Bradley Horrocks||86 - 80||James Kennedy||Nick Hewer||Rachel Riley||Paul Zenon||Susie Dent||121|