He currently plays for Waterford United, wearing the number 14 shirt. He plays primarily as a Defender. His current market value is estimated at 75K €.

His most recent move was a from Lecce Primavera to Waterford United on 2024-07-13.

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.