 On 31 January, he was presented with the Ladbrokes Scottish Championship Player of the Month award for January 2019.On 10 February, in the next round of the Scottish Cup, he scored an "outrageous" goal from around 30 yards to equalise against Aberdeen at Pittodrie, although this time the top-tier side responded and eventually won 4–1 to eliminate Queen of the South from the competition.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.