On 11 May 2019, Dobbie scored his tenth hat-trick since his return to the "Doonhamers", this time in a 5–0 win at home to Montrose in the Scottish Championship play-off semi final second leg, his sixth treble of the season. Dobbie scored his goals after 11, 28 and 40 minutes. Dobbie has scored the most goals for the "Doonhamers" in all competitions in a single season in their 100-year history. The previous record of 41 goals was held between Jimmy Rutherford in 1931–32 and Nicky Clark in 2012–13. Dobbie scored 43 goals (21 league and 22 cup) in his third season back in Dumfries.