 On 9 October 2018, Dobbie signed an extension to his contract to keep him at the Dumfries club until May 2020.On 29 January 2019, Dobbie scored his ninth hat-trick since his return to the "Doonhamers", this time in a 3–0 win at home to Scottish Premiership club Dundee, in the fourth round replay of the 2018–19 Scottish Cup, his fifth treble of the season.Dobbie scored his goals after 12, 27 and 74 minutes, the first being a "looping long-range effort" from 25 yards.