Nicknamed "The Human Dictionary", he made his debut on 22 November 2019 against Paul Anderson, winning the game on a tiebreak conundrum. He then put in 7 sensational performances scoring 7 centuries. He wrapped up his heat run with 899 points to become an octochamp — the final of a record nine to have appeared in the series.
Ten days later, the Human Dictionary 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 he dodged a crucial conundrum and confirmed a finals spot against #1 contender James Haughton.
In the final Wing played real 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 points. Wing amassed 1,206 points in his run.
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|7211||22/11/2019||P||Paul Anderson||90 – 100*||Jamie Wing||Tanni Grey-Thompson||Susie Dent||134|
|7212||25/11/2019||P||Jamie Wing||117 – 23||Sharif Dougramaji||Tanni Grey-Thompson||Susie Dent||126|
|7213||26/11/2019||P||Jamie Wing||114 – 53||Greg Folgate||Tanni Grey-Thompson||Susie Dent||135|
|7214||27/11/2019||P||Jamie Wing||120 – 62||Peter Jackson||Tanni Grey-Thompson||Susie Dent||147|
|7215||28/11/2019||P||Jamie Wing||118 – 68||Alan Jones||Hannah Fry||Susie Dent||129|
|7216||29/11/2019||P||Jamie Wing||122 – 44||Barbara Wylde||Hannah Fry||Susie Dent||132|
|7217||2/12/2019||P||Jamie Wing||96 – 53||Joseph Bennett||Hannah Fry||Susie Dent||138|
|7218||3/12/2019||P||Jamie Wing||122 – 86||Alex Stuart||Hannah Fry||Susie Dent||148|
|7226||13/12/2019||QF||Jamie Wing||121 – 78||Tom Silverlock||Jon Culshaw||Susie Dent||146|
|7230||19/12/2019||SF||Jamie Wing||91 – 77||Paul Nixon||Tim Vine||Susie Dent||125|
|7231||20/12/2019||GF||James Haughton||110 – 95||Jamie Wing||Tim Vine||Susie Dent||125|