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.
The passage describes Dobbie's consistent success during his time in the Scottish Championship, receiving multiple nominations and awards for his performance.