Benning featured 55 times over the course of the 2018–19 season, missing just one league game. Mansfield finished in fourth place but were beaten on penalties by Newport County in the semi-finals of the play-offs despite Benning converting his penalty. Flitcroft was sacked after the defeat, though Benning said that he was ready to focus on football again after returning from holiday in Mexico and that he and the rest of the squad had had positive meetings with new manager John Dempster. However, the new season went poorly and Dempster was replaced by Graham Coughlan in December. Benning played 39 games in the 2019–20 season, which saw Mansfield finished 21st on points per game after the season was curtailed early due to the COVID-19 pandemic in England.