Crawley is a right-handed batsman, and an occasional wicket-keeper. His main strengths are his batting against spin bowling and his leg side stroke play.
He made his first-class debut for Lancashire in the 1990 season. During his time as a university student, he played first-class cricket for both Lancashire and Cambridge University. After graduation he turned professional and stayed on at Lancashire.
Crawley began to produce a number of impressive innings. In 1993, he scored 109 for Lancashire as they defeated a strong Australian cricket team in a tour match. The tourists' team had included Shane Warne and Merv Hughes, and Crawley's performance moved the Australian coach Bob Simpson to label him the best batsman they had played against that summer. This was during the 1993 Ashes series in which Australia comfortably defeated England.
Having impressed the selectors, he was chosen to play for England during the 1994 Test series against South Africa. However, he struggled against the South African pace bowling attack who exposed a weakness on his off side.
Despite his poor start to international cricket, Crawley was selected in the touring squad for the 1994-95 Ashes series in Australia. He produced his first substantial innings for England scoring two 70s in the 3rd and 4th Tests of the series, but got a pair in the 5th. During the tour, he was criticised for being overweight – an issue he resolved for the following season.
Crawley was in-and-out of the England team over the next few years. In 1996 he scored 106 against Pakistan, his first Test century, and in 1998 he scored 156 not out against Sri Lanka, his highest Test score. However, a poor performance during the 1998-99 Ashes series led to him being dropped from the side, apparently for good.
In the absence of the suspended Shane Warne, Crawley captained Hampshire during the 2003 season. He continued to score heavily in county cricket for Hampshire. His highest first-class score is 311 not out, scored in September 2005 against Nottinghamshire, beating his previous best of 301 not out which he reached in 2004 also against Nottinghamshire. Crawley was awarded a benefit year for the 2008 County Championship.