[18] His father's business, which eventually developed into a motor vehicle garage, was doing well by the time Woolley was a teenager, and Frank had the opportunity to attend the fee-paying Tonbridge School.

[23] Blythe had been Woolley's childhood hero[17] and he appears to have modelled his bowling action on the older man, holding his bowling arm behind his back as he approached the wicket—Woolley's biographer Ian Peebles suggested that the main difference was that Woolley's left-arm came from his hip pocket rather than from his right armpit as Blythe's had done.

[23] His first-class cricket debut was marked by a third-ball duck, dropping Johnny Tyldesley, who scored 295 not out, three times and taking just one wicket in Lancashire's first innings.

[10][16][26] In Kent's second innings however, he scored 64 runs and he retained his place in the side for most of the remainder of the season, only dropping out of the First XI during Canterbury Cricket Week, a significant social occasion when amateur batsmen were more likely to make themselves available to play.

[26] He took his first five-wicket haul in his second match against Somerset at Gravesend,[16] before a fine all-round performance against Surrey at The Oval in his third match–eight wickets, including five wickets for 80 runs (5/80) in Surrey's second innings, and scores of 72 and 26 not out won the match for Kent and established Woolley's reputation as a young player of significant promise.

[d][31] His total of 58,959 runs[a] is the second highest of all time in first-class matches, beaten only by Jack Hobbs,[10] and his 145 centuries is seventh on the all-time list.

[41][42] Writing for Barclay's World of Cricket, Harry Altham described Woolley as a "tall and graceful" figure who, with "a quiet air" was "unhurried in his movements".

[43] As a batsman, he had a gift for timing his shots and made full use of his long reach; he was especially strong in driving off his back foot against balls that other batsmen might consider good length deliveries.

Altham pointed out that, although Woolley lacked the subtlety of Wilfred Rhodes, he was nevertheless a formidable bowler on any pitch whose conditions helped him.

"[49] After the outbreak of World War I in August 1914 the English cricket season continued, although public interest declined and the social side of the game was curtailed.

[50] Woolley was married in September and did not immediately join the armed forces, instead working in his father's workshop which had been converted to manufacture munitions.

[h][31] He was recruited by Jack Hobbs, also working in the munitions industry, to play for Keighley in the Bradford Cricket League[54] and made a number of appearances in exhibition matches, including making a century for a Lancashire side against Yorkshire during 1916.

[6][32][51] He was transferred to the RAF Reserve in January 1919 before being officially discharged in 1920;[32] during 1922 he played a single first-class match for the Royal Air Force cricket team.

[55] His only son, Richard, died whilst serving as a merchant seaman on SS Beaverford as part of Convoy HX 84 in November 1940,[52][55] and the house in Cliftonville was destroyed in a bombing raid in 1941.

[56] During the war Woolley played in a number of exhibition matches designed to entertain the public and help boost morale.

[56] He remained active, regularly visiting the St Lawrence Ground during Canterbury Cricket Week,[26] and in January 1971 he flew to Australia to watch the last two Tests of the 1970–71 Ashes series.

[49] Later in the year he married an American widow, Martha Wilson Morse and set up home in the Canadian Province of Nova Scotia.