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 3.5 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||Guest||Lex||Max|
|2843||20/09/2000||P||Iain Macdonald||58 – 40||James Kennedy||Geoffrey Durham||Damian Eadie||74|
|6690||18/10/2017||P||Alex Smith||73 – 80||James Kennedy||Adrian Chiles||Susie Dent||132|
|6691||19/10/2017||P||James Kennedy||105 – 39||Krishna Shukla||Adrian Chiles||Susie Dent||136|
|6692||20/10/2017||P||James Kennedy||88 – 41||Dylan Henderson||Adrian Chiles||Susie Dent||137|
|6693||23/10/2017||P||James Kennedy||83 – 82||Rania Abdul-Wahab||Adrian Chiles||Susie Dent||135|
|6694||24/10/2017||P||James Kennedy||99 – 46||Ian Currie||Adrian Chiles||Susie Dent||132|
|6695||25/10/2017||P||James Kennedy||95 – 80||John Oxley||John Challis||Susie Dent||146|
|6696||26/10/2017||P||James Kennedy||94 – 61||Mary Anderson||John Challis||Susie Dent||125|
|6697||27/10/2017||P||James Kennedy||92 – 52||Charlie Turner||John Challis||Susie Dent||113|
|6731||15/12/2017||QF||Bradley Horrocks||86 – 80||James Kennedy||Paul Zenon||Susie Dent||121|