Will Dennis

Early career

Dennis started his career in the academy of Luton Town before moving to join the Watford academy, where he played from under-9s up to under-16s. After being released by Watford, Dennis had trials with Milton Keynes Dons, Coventry City and Stevenage.

AFC Bournemouth

Dennis joined Bournemouth at the age of 15 in 2016, turning professional 18 months later and joining the first-team at the start of the 2019–20 season. He also had spells in non-league with Guernsey and Weymouth during the 2017–18 season. In March 2020 he signed a new three-and-a-half-year contract with the club. Later that month he was praised by manager Eddie Howe. On 11 December 2021, Dennis signed for Wealdstone on an emergency loan. He made his debut on the same day, in a 1–0 defeat to Halifax On 18 December 2021, Dennis was recalled from his loan spell by parent club Bournemouth. In January 2023, Dennis joined National League South club Slough Town on loan for the remainder of the season. In June 2023 he signed on loan for Kilmarnock for the season. In February 2026 he moved on loan to Leyton Orient.

Milton Keynes Dons

On 26 August 2026, Dennis joined League One club Milton Keynes Dons on a permanent deal, signing a three-year contract for an undisclosed fee.

As of 6 October 2026