In August 2018, Dempsey moved to Peterborough United on a season-long loan before signing for Gillingham on a permanent deal in January 2019. After a successful spell at Gillingham, Dempsey signed for Bolton Wanderers in July 2021.
In August 2018, Dempsey moved to Peterborough United on a season-long loan before signing for Gillingham on a permanent deal in January 2019. After a successful spell at Gillingham, Dempsey signed for Bolton Wanderers in July 2021.