|Conundrums solved||6 (+1 tiebreak)|
Wing made his debut, aged 17, on 22 November 2019 against six-time winner and fellow Apterite Paul Anderson, winning the game on a tiebreak conundrum. He then put in 7 sensational performances scoring 6 centuries. He wrapped up his heat run with 899 points to become an octochamp — the last of a record nine to have appeared in the series.
Ten days later, Wing returned for the series finals, starting his finals run against number 7 seed Tom Silverlock. Wing proved unstoppable here, by scoring in every letters and numbers round and pulling away with a very good 6-small solve plus a spot of the nine-letter word ROUTINISE. His only no-score occurred in the conundrum, which Silverlock beat him to, but a strong 121 points booked Wing a place in the semi-finals. He next squared off against Paul Nixon, the number 3 seed; though the game's score was dead level from the first break straight up to before the final letters, PACEMEN and a one-away solve on a complex six-small selection meant that Wing avoided a crucial conundrum and confirmed a finals spot against number 1 contender James Haughton.
In the final, Wing played close to Haughton. They levelled in the first two letter rounds until Haughton nicked the lead with the first numbers round. Wing, however, stayed close to Haughton throughout the game and as a last consolation solved the conundrum, TREATRASH to EARTHSTAR, to finish in the runner-up position with 95 points, while Haughton won with 110. Wing amassed 1,206 points in his run.
He did not participate in Championship of Champions XVI, thus preserving his record of 10 wins out of 11.
|#||Date||Type||Contestant 1||Score||Contestant 2||Presenters||Guest||Lex||Max|
|7211||22/11/2019||P||Paul Anderson||90 - 100*||Jamie Wing||Nick Hewer||Rachel Riley||Tanni Grey-Thompson||Susie Dent||134|
|7212||25/11/2019||P||Jamie Wing||117 - 23||Sharif Dougramaji||Nick Hewer||Rachel Riley||Tanni Grey-Thompson||Susie Dent||126|
|7213||26/11/2019||P||Jamie Wing||114 - 53||Greg Folgate||Nick Hewer||Rachel Riley||Tanni Grey-Thompson||Susie Dent||135|
|7214||27/11/2019||P||Jamie Wing||120 - 62||Peter Jackson||Nick Hewer||Rachel Riley||Tanni Grey-Thompson||Susie Dent||147|
|7215||28/11/2019||P||Jamie Wing||118 - 68||Alan Jones||Nick Hewer||Rachel Riley||Hannah Fry||Susie Dent||129|
|7216||29/11/2019||P||Jamie Wing||122 - 44||Barbara Wylde||Nick Hewer||Rachel Riley||Hannah Fry||Susie Dent||132|
|7217||2/12/2019||P||Jamie Wing||96 - 53||Joseph Bennett||Nick Hewer||Rachel Riley||Hannah Fry||Susie Dent||138|
|7218||3/12/2019||P||Jamie Wing||122 - 86||Alex Stuart||Nick Hewer||Rachel Riley||Hannah Fry||Susie Dent||148|
|7226||13/12/2019||QF||Jamie Wing||121 - 78||Tom Silverlock||Nick Hewer||Rachel Riley||Jon Culshaw||Susie Dent||146|
|7230||19/12/2019||SF||Jamie Wing||91 - 77||Paul Nixon||Nick Hewer||Rachel Riley||Tim Vine||Susie Dent||125|
|7231||20/12/2019||GF||James Haughton||110 - 95||Jamie Wing||Nick Hewer||Rachel Riley||Tim Vine||Susie Dent||125|