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.
[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.
[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.
[22] Though included in most matchday squads,[8] Gilbert appeared sparingly during the first three months of the 2024–25 season, before breaking into the team in a substitute role.
[23] He made 10 appearances and scored one goal prior to departing to join League One club Charlton Athletic on loan until the end of the 2024–25 season on the final day of the winter transfer window.