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On 16 February 2019, Woolfenden signed a new 3 year contract with the club, with the option of an additional year’s extension. After returning from loan, Woolfenden became a regular player for Ipswich during the 2019–20 season following relegation to League One the previous season. On 25 January 2020, he scored his first goal for the club, netting the winner in a 1–0 win against Lincoln City at Portman Road.

In December 2017 he joined Bromley on a month's loan. He made his debut for Bromley against Macclesfield Town on 23 December. On 27 April 2018, Woolfenden was recalled from his loan spell at Bromley. He made 17 starts and three sub appearances, scoring once, for the Ravens having joined them just before Christmas.

On 31 August 2018, Woolfenden joined League Two side Swindon Town on loan until the end of the season. He scored his first goal for the club in a 1–2 loss to Bury on 15 September 2018. Woolfenden made 36 appearances in all competitions during his loan spell at the County Ground, scoring two goals.

Woolfenden joined the Ipswich Town academy as a Schoolboy player at the age of 11, he then became a full academy player with Town in July 2015, signing a two-year scholarship, before he signed his first professional contract for the 2017–18 season. He went on to make his full senior debut in a 2–0 win over Luton Town in the League Cup first round on 8 August 2017. On 28 April 2018, Woolfenden made his full championship debut for Ipswich Town away to Reading. Ipswich Town went onto win the game 4-0, with Woolfenden playing the full game. He would also come on as a substitute in the last game of the 2017–2018 season in the 2-2 home draw against Middlesbrough.

Luke Matthew Woolfenden (born 21 October 1998) is an English professional footballer who plays as a defender for Ipswich Town. Primarily a centre back, he can also play as a right back.