Crawley played cricket whilst at Manchester Grammar School where he broke a number of batting records previously held by Mike Atherton. After finishing school, he continued his education at Trinity College, Cambridge.

Crawley played as a paid amateur for Farnworth CC in the Bolton League before moving on to bigger things with Lancashire County Cricket Club. 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, becoming team captain in 1999–2001.

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. In 1994, he was named Young Cricketer of the Year by the Cricket Writers' Association.

Crawley was selected for the England A team to tour South Africa that winter. In one tour match, he scored 286 against Eastern Province. He followed this up with 281 not out against Somerset the following season.

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 2002, Crawley moved from Lancashire to Hampshire, scoring 272 on his debut, and with an average of over 100 after the first three games he was recalled for Sri Lanka's tour in England. Over the next year he was used as first reserve, and in January 2003 played his last Test match – England's fifth Test victory over Australia at Sydney.

In the absence of the suspended Shane Warne, Crawley captained Hamp