Woakes was born in March 1989 in Birmingham, and attended Barr Beacon Language College in Walsall from 2000 to 2007. He began playing cricket when he was seven years old with Aston Manor Cricket Club. He played three games in the 2006 Minor Counties Trophy for Herefordshire County Cricket Club, and played for Warwickshire’s under-15, under-17, Academy and Second XI teams between 2004 and 2007. He was a trainee footballer with Walsall F.C. as a winger until the age of 14.

He was a regular for the Warwickshire First XI in 2008. He took 42 wickets at an average of 20.57 runs per wicket over the course of the County Championship season, topping Warwickshire’s bowling averages.

On 6 April 2009, Woakes was called up to the England Cricket squad for the World Twenty20 in June. Allan Donald tipped Woakes as a future England international cricketer. Woakes was then chosen to play for the England Lions in a warm-up match against the West Indies. In the first innings, he achieved bowling figures of 6–43 (including the wickets of Ramnaresh Sarwan and Shivnarine Chanderpaul) as the West Indies were bowled out for 203. During the same season he scored 131 not out against Hampshire, his maiden first-class century, batting at number nine and sharing a 222-run partnership with Jonathan Trott. In an England Lions game against Australia Woakes was able to pick up the wickets of Ricky Ponting and Mike Hussey.

Woakes claimed his 200th first-class wicket in Warwickshire’s victory over Sussex in the County Championship in July 2011. In the 2020 IPL auction, he was bought by the Delhi Capitals ahead of the 2020 Indian Premier League. However he pulled out of the 2020 IPL to keep himself up and running for the English summer.He was replaced by South African seamer Anrich Nortje.

Woakes made his International Twenty20 debut on 12 January 2011 against Australia in Adelaide. Opening the bowling, he took figures of 1/34, taking the wicket of Australian captain Cameron White with his final delivery. He later scored the winning runs, as England won off the last ball with just one wicket left and one run required. In the second match he made 11 not out and took 1–29 with the ball. He featured in the third ODI, taking 1–31 as England lost by 4 wickets. In just his second ODI Woakes took figures of 6–45, although England went on to lose the game by 45 runs. He kept his place for the next game, but was less impressive, finishing with 0–73. He was selected for the T20 against Sri Lanka, although he managed only 7 runs and finished wicketless.

Woakes returned to the England set up in 2012 for the 2nd ODI against South Africa, although the match was rained off. He returned for the fifth ODI, scoring an unbeaten 33 as England lost by 7 wickets.

On 21 June 2016, he scored his highest ODI score of unbeaten 95 runs in the first ODI against Sri Lanka. His score is the highest ODI score by number eight or lower in ODI history. Finally the match was ended with a tie and Woakes adjudged man of the match. In the second ODI he did not take a wicket but bowled economically as England won by ten wickets. He took 3–34 in the third match of the series, which was eventually abandoned due to rain. He did not take wicket in the fourth match of the series, finishing with figures of 0–65, although England went on to win the game. In the final game of the series he scored an unbeaten 17 to help England to 324/7, and they went on to win the match by 122 runs to win the series 3–0.

In April 2019, he was named in England’s squad for the 2019 Cricket World Cup. He won Man of the Match in the 2019 World Cup semi-final against Australia taking 3 wickets to see England through to the World Cup Final against New Zealand for the first time since 1992. Woakes again took 3 wickets in the final as England would go on to win the World Cup.

On 29 May 2020, Woakes was named in a 55-man group of players to begin training ahead of international fixtures starting in England following the COVID-19 pandemic. On 17 June 2020, Woakes was included in England’s 30-man squad to start training behind closed doors for the Test series against the West Indies. On 4 July 2020, Woakes was named in England’s thirteen-man squad for the first Test match of the series. In the second Test, Woakes took his 100th wicket in Test matches.