He narrowly progressed through qualifying against Zak Eadle, before losing in the first round of the main draw to Craig Greenhalgh.

Shenkman again played for the British Team at the Van Alen and Limb Cups at Manchester, winning both of his singles matches.

In early 2020, he travelled to Australia as a hitting partner for Ben Taylor-Matthews in the 2020 World Championship Eliminator.

There, he and Taylor-Matthews began their podcast "A View from the Hazards,"[9] which they continued through the subsequent hiatus from competitive play due to COVID-19.

In 2022, he won the US Amateur Championships for the first time, and progressed through qualifying to reach the main draw of the US Open.

He also debuted at the French Open, winning a set off former World Champion Robert Fahey in the first round.

[12] Shenkman would lose in the quarter final to Leon Smart 6/5 6/5 6/5, but he would win the associated Satellite tournament as a consolation prize.

Shenkman occasionally competes in rackets tournaments, most notably at the Manchester Gold Racquet each year since 2014, excluding 2018.

He has reached the semi final on two occasions, losing to Alexander Duncliffe-Vines in 2019 and then-future World Champion Ben Cawston in 2022.