In 2012, Crichlow left Bermuda to join the youth academy of Spanish side Cornellà.
[5] In May 2019, it was announced that Crichlow would join Watford in July from AFC Wimbledon, signing a two-year contract.
[6] Crichlow made his professional debut for Watford on 22 September 2020 as a substitute in the EFL Cup against Newport County.
[10] In January 2024, he scored five goals in a single game against Aldershot Town in the FA Trophy.
[6] In March 2021, he was called up by Bermuda for their CONCACAF Group B qualifiers against Canada and Aruba later that month.