[3] In April 2016, whilst still an under-18 player, he joined local Isthmian League Division One South side Worthing on a youth loan until the end of the season.
[8] He continued to remain a first team regular and helped Dagenham to a fifth-place finish where they eventually lost out to Forest Green Rovers in the play-off semi-finals.
[9] He made a total of forty-eight appearances for the Daggers, scoring sixteen times and won the Young Player of the Year award.
[25] A month later Maguire-Drew officially departed Grimsby by mutual consent,[26] and subsequently joined Yeovil Town permanently signing an 18-month contract.
[27] On 22 December 2023, Maguire-Drew joined National League side Barnet on loan until the end of the 2023–24 season, with the option of a free permanent transfer subject to terms.
[28] In September 2024, Maguire-Drew had his contract mutually terminated with Yeovil and subsequently signed for National League South side Weymouth.