On 24 April 2019, Dobbie was nominated for the PFA Scotland's Championship player of the season, for the third consecutive year, alongside Billy Mckay, Lawrence Shankland and Pavol Šafranko and on 5 May 2019, Dobbie won the individual award and was selected in the Championship Team of the Year for the third successive season. He also won the equivalent individual award presented by the SPFL. Despite Dobbie's personal achievements, Queens finished ninth in the 2018–19 Scottish Championship and entered the play-offs along with Forfar Athletic, Raith Rovers and Montrose from League One.