He currently plays for Fleetwood Town, wearing the number 36 shirt. He plays primarily as a Defender. His preferred foot is Left. His current market value is estimated at 75K .

His most recent move was a Transfer from Waterford United to Fleetwood Town on 2026-07-31.

Throughout the Ireland Premier Division 2026, Jesse Dempsey featured in 4 matches, averaging 0 tackles, 0 interceptions, and 0 clearances per game, while blocking 0 shots per game.