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.
In April 2019, Dobbie was nominated for PFA Scotland's Championship player of the season for the third year in a row, alongside Billy Mckay, Lawrence Shankland, and Pavol Šafranko. He then won the individual award on May 5th, 2019, and was selected to the Championship Team of the Year for the third consecutive season.