[2] Crawley was born in Bromley in south-east London and was educated at New Beacon School in Sevenoaks and Tonbridge School;[3][4] his father Terry is a retired City of London futures trader who had begun his working life as a carpet fitter, before becoming one of Britain's highest-paid men and making the Sunday Times Rich List following his change of profession.

[22] The match ended in controversial circumstances with the opposing Leeward Islands bowling wide balls in what was seen by some as an attempt to deny Crawley the opportunity to reach his century.

[23] During the 2018 season, Crawley became a regular in the Kent side, playing in all of the team's first-class matches as well as occasional limited overs games.

[28] Crawley was drafted by London Spirit for the inaugural season of The Hundred, but only featured once, scoring 64 as an opening batsman in a loss to Birmingham Phoenix.

[34][38][39] After scoring a century in a warm-up match,[40][41] Crawley was brought into the team for the second Test following an injury to Jos Buttler, making his debut at Seddon Park on 29 November aged 21.

[42] After scoring only one run on debut, batting at number 6, he was retained in the squad for the tour of South Africa in December and January.

His "excellent temperament"[43] and "unflustered" approach were praised as was his bravery against short-pitched bowling,[44] although some technical issues with his batting were also commented on.

[71][72] He lost his place in the team during the summer, but his central contract was renewed and he was retained in the squad for the 2021–22 Ashes series in Australia.

[73][75] A score of 77 runs from 100 balls in the fourth Test saw him retain his place for the remainder of the five-match series,[76][77] and he was selected to tour the West Indies in early 2022.

Crawley scored his second Test century during the first match of the West Indies tour,[71] and his innings of 121 saw Viv Richards describe him as "a magnificent player".

[78][79] His performances in the other two matches of the series, however, led to critics questioning his shot selection, especially outside off stump, with the perception that he needed to address his tendency to be out playing an off drive, particularly when the ball is swinging.