 Dobbie scored 43 goals (21 league and 22 cup) in his third season back in Dumfries.On 27 July 2019, Dobbie was not in the squad for the final Scottish League Cup Group E match at Cappielow versus Greenock Morton, as he was injured early in the second half in the previous match away to Dumbarton.On 19 October 2019, after a wood carving statue of three club legends, Dobbie alongside Allan Ball and Billy Houliston was unveiled outside the Queens Arena to mark Queens Centenary season, Dobbie scored a brace as the "Doonhamers" resoundingly defeated league leaders Dundee United 4–0 at Palmerston Park.