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Iffy Allen began his career at Fulham as a 14-year-old, where he spent a year in the youth team before being released. He also had a trial with Reading, and then joined Barnet in the summer of 2010, signing a two-year scholarship.
He debuted for the Bees as a 73rd-minute substitute in an FA Cup first-round tie at home to Oxford United on 3 November 2012. In January 2013, Iffy signed a “long-term” professional contract with the Bees.
Iffy scored his first goal for Barnet in a 3–3 draw at Lincoln City on the final day of the 2013/14 season. He joined Wingate & Finchley on a three-month loan and was released by Barnet at the end of the 2014/15 season.
Following his release from Barnet, he signed for League Two side Yeovil Town on a one-year deal. He then went on to play for Torquay United, Aldershot Town, Wrexham, and Bromley.
Iffy Allen joined Dulwich Hamlet in September 2018 and signed for Braintree Town in January 2019. He then joined Maidstone United for the 2019/20 season and then played for Ebbsfleet United in the curtailed 2020/21 season. He joined Lewes in August 2021 and in February 2022, he joined National League South side Hampton & Richmond Borough. He then joined Carshalton Athletic in August 2022.
On 17 July 2023, Allen signed for National League South club Dover Athletic. Following relegation, he was released at the end of the 2023/24 season.
Iffy signed for The Saints in the summer of 2024.
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