West Bromwich Albion

An attacking midfielder,^[3] Gilbert began his career in the West Bromwich Albion Academy at U9 level and progressed to sign a two-year scholarship deal in 2018.^[4] He was offered a professional contract at the end of the 2019–20 season, but declined to sign it and departed The Hawthorns.^[5]

Brentford

On 29 September 2020, Gilbert transferred to the B team at Championship club Brentford on a two-year contract, with the option of a further year,^[6] on a free transfer.^[7] Gilbert was an unused substitute during 9 first team league matches between December 2020 and March 2021 and made what would be his only first team appearances for the club with two FA Cup appearances.^[8] He was not involved during Brentford's successful 2021 playoff campaign and finished the 2020–21 B team season with 10 goals from 22 appearances.^[8][9][10]

Gilbert was involved with the first team squad during the 2021–22 pre-season and on transfer deadline day August 2021, he joined League Two club Swindon Town on loan until the end of the 2021–22 season.^[10] He made 12 appearances prior to the termination of the loan on 4 January 2022.^[11] Gilbert played the second half of the 2021–22 season with the B team,^[11] with whom he won the London Senior Cup.^[12]

The one-year option on Gilbert's contract was taken up at the end of the 2021–22 season and he captained the B team during the 2022–23 season.^[13][14] On 8 November 2022, Gilbert won his first senior call-up for nearly two years, for an EFL Cup third round match versus Gillingham and he remained an unused substitute during the shoot-out defeat.^[8] He was included in the first team squad for its mid-season training camp in Girona and scored in a 2–1 friendly defeat to Bordeaux.^[15] Half of Gilbert's 16 goals scored during the B team season came in the team's victorious 2022–23 Premier League Cup campaign.^[8][16] His performances were recognised with the team's Player of the Year award.^[17]

Gilbert entered discussions over a contract extension at the end of the 2022–23 season,^[18] which proved fruitless.^[14] He departed the club in July 2023 and finished his B team career with 79 appearances.^[14]

Middlesbrough

On 4 July 2023, Gilbert transferred to Championship club Middlesbrough and signed a four-year contract.^[19] Though he was signed as a free agent, the club was required to pay a compensation fee of "around £1 million", due to his age.^[20]