Kashket began his career playing futsal for Maccabi GB in the English National Futsal League, and had played for the Great Britain junior futsal team at the European Maccabiah Games in Vienna in 2009. He was spotted and signed by Spanish club Hércules, and played for their 16–19 and 18–21 age group football teams in late 2012. On his return to the UK, he played for the Wingate & Finchley U21 team, scoring three goals in two matches during October 2013. Later in 2013, Kashket had a trial with Maccabi Tel Aviv, but suffered an injury on his first day with the club. By this time he was training and playing with Leyton Orient's youth team.
After impressing in the Orient youth team, Kashket signed a two-year professional contract with the club in the summer of 2014, while still featuring for the youth team. He scored a penalty in Orient's 3–2 friendly win at Dartford on 18 July, and came on as a substitute in the 1–0 friendly win at Northampton Town on 26 July, and the 2–2 draw with Queens Park Rangers on 29 July. Kashket was an unused substitute for Orient in several matches in the early part of the 2014–15 season, and made his professional debut as a late substitute for Jay Simpson in the 2–0 league defeat at home to Preston North End on 29 October, which was manager Mauro Milanese's first match in charge of the club. On 11 November, he was brought on as a substitute early in the second half in Orient's 2–0 Football League Trophy southern section quarter-final win against Northampton Town. Kashket made his first start for Orient on 11 August 2015, playing the full 90 minutes of the 2–1 League Cup defeat at MK Dons. He scored his first senior goal in the 2–2 draw at home to Oxford United on 17 October, coming on as a substitute for John Marquis and grabbing a last-minute equaliser. On 4 March 2016, he moved to Welling United on a one-month loan.
Wycombe Wanderers
Following his release from Leyton Orient, Kashket signed a four-month deal with Wycombe Wanderers on 31 August 2016. He scored his first goals for Wycombe when he scored twice in a 5–1 win over Crewe Alexandra on 27 September 2016. He signed a new three-year contract with Wycombe in May 2019.
