[5] Dundee's pre-season schedule would include a week-long camp in Ireland and playing Bray Wanderers and Fleetwood Town while there, as well as two visits to local Angus teams in Brechin City and Arbroath, followed by an away game against Cove Rangers.

Despite managing a 1–0 win over their historical bogey team, Dundee would exit the League Cup in the group stage for the first time since the 2016–17 season via goals scored.

[12] On their flag-raising day returning to the top tier, Dundee would come back from behind through a Lyall Cameron goal to draw with Motherwell at a rain-drenched Dens Park.

[14] After a two-week hiatus, Dundee grabbed their first win of the league season at home to Hearts through a Luke McCowan chip over Zander Clark from distance.

[30][31] The pitch was fine however on Boxing Day with Celtic visiting, and despite keeping a clean sheet in the first half Dundee once again capitulated to a standard home defeat to the Hoops.

[38] Dundee would end the month by finally playing Aberdeen for the first time of the season, and a Lee Ashcroft headed goal off a corner from the returning Owen Beck was enough to earn a point at Pittodrie.

[41] Despite a slow start, a Luke McCowan penalty and a Jordan McGhee header provided a much-needed comeback win to consolidate Dundee's position in the top 6 at home against St Johnstone.

[45] The Dee would again play an evenly-matched game against Europe-chasing Kilmarnock, and despite leading late against ten men they again dropped points in stoppage time in a third consecutive 2–2 draw against the Ayrshire side.

[46] After an extended break, Dundee returned in solid form despite injuries and comfortably defeated managerless Aberdeen through a Luke McCowan penalty, lifting the Dees back into the top six after keeping their first clean sheet against the Dons in almost 20 years.

[48] After the international break, Dundee returned with a vengeance to McDiarmid Park, and despite looking second best to St Johnstone in large parts they brought home all 3 points through two clinical strikes.

[50][51] After much controversy regarding the playability of Dens Park's pitch, Dundee would take on Motherwell in a chaotic affair, with a 2-goal lead in the second half not being good enough for the fourth time this season as the visitors snatched all three points late and denied the Dee from securing a top six place.

[53] Though a strong 2nd half showing at Pittodrie was not enough to break a goalless deadlock against Aberdeen (their first clean sheet against the Dons since December 2004), a late equaliser for Motherwell over Hibs ensured that Dundee's point would be enough for them to secure top six football with a game to spare.

[65] On a glorious sunny May day at Dens, Dundee ended their season with yet another draw against Kilmarnock as the home side couldn't find a winner against 10 men, with player of the year Luke McCowan knocking a late penalty to win the game wide of the post.