Osmond first appeared on 21 October 2019 against Pierse Walsh and won with a tight 82-77 points. He followed this with several more close performance including two centuries. He wrapped his heat run with a total of 711 points to become an octochamp and returned for the finals in December 2019, as 6th seed to face number 3 seed Paul Nixon in the third quarterfinal.
In his quarterfinal against Nixon, Osmond fought hard and at one point maintained a two point lead. However Nixon fought back and solved the conundrum, relegating Osmond to his first defeat. Osmond garnered an overall total of 813 points in his run.
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|7187||21/10/2019||P||Pierse Walsh||77 – 82||John Osmond||Gloria Hunniford||Susie Dent||148|
|7188||22/10/2019||P||John Osmond||68 – 65||Vamsi Pratapa||Gloria Hunniford||Susie Dent||132|
|7189||23/10/2019||P||John Osmond||77 – 53||Colin Mason||Gloria Hunniford||Susie Dent||146|
|7190||24/10/2019||P||John Osmond||109 – 24||Ben Pooley||Levi Roots||Susie Dent||143|
|7191||25/10/2019||P||John Osmond||119 – 22||Ann Wagstaff||Levi Roots||Susie Dent||135|
|7192||28/10/2019||P||John Osmond||78 – 44||Catherine Oliver||Levi Roots||Susie Dent||125|
|7193||29/10/2019||P||John Osmond||95 – 94||Mike Woodberry||Levi Roots||Susie Dent||164|
|7194||30/10/2019||P||John Osmond||83 – 62||Toby Pleming||Levi Roots||Susie Dent||125|
|7227||16/12/2019||QF||Paul Nixon||117 – 102||John Osmond||Jon Culshaw||Susie Dent||158|