Crawley began his cricketing journey at a young age, playing for Kent in domestic competitions. He made his debut for Kent in 2017 and quickly gained recognition for his technical prowess and calm demeanor at the crease. His consistent performances in county cricket led to his selection for the England national team, and he made his Test debut against New Zealand in November 2019. Crawley is known for his elegant stroke play and ability to score big runs. One of his most notable innings came in August 2020, when he scored a double century (267 runs) against Pakistan, showcasing his potential as a top-order batsman.