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. On 21 December 2019, Dobbie extended his contract at Queens until 31 May 2021.