[4][5] Dundee would start their competitive season off with a comfortable 3–0 win over fellow Championship side Hamilton Academical in the League Cup group stages.

[10] Despite their strong start to the season, Dundee would struggle badly in the league opener against Partick Thistle, scoring 2 late goals but still losing 2–3.

[12] They would continue their momentum with a gritty and impressive win over Arbroath to go top of the table, on an emotional night which commemorated the recently-passed Dundee legend Pat Liney.

[27] The month started off improbably for Dundee they came back from a two-goal deficit against Partick Thistle to win in dramatic fashion at Firhill Stadium.

[28] They would continue this positive momentum the following week, with Zach Robinson running the show and scoring both goals in a big home win over in-form Raith Rovers.

[36] Dundee would end the year with yet more cheer, topping the league for Christmas after a double by Luke McCowan against his former club Ayr United clinched a win to pip the Honest Men to top spot despite an early straight red for Josh Mulligan, marking Dundee's seventh consecutive win in all competitions, their first such run since February 1974, as well as their fourth consecutive league clean sheet, and fifth in their last 6 games in all competitions.

[37] Dundee's momentum came to a screeching halt in the new year, and despite coming back from 2 goals and a man down they would suffer defeat against part-time Arbroath, knocking them off top spot.

[40] They would finally play a home game the following Tuesday in the Scottish Challenge Cup quarter-finals, defeating League One leaders Dunfermline Athletic (managed by former Dundee boss James McPake) to progress to the semi-finals in a high-scoring affair.

[41][42] Despite being dogged by injuries and disjointed by squad changes, Dundee comfortably beat league leaders Queen's Park to end the month on a high note.

[43] Dundee opened up the month in frustrating fashion, failing to capitalise on chances and having to settle for a point against bottom side (albeit in good form) Hamilton Accies.

[44] They then somehow snatched defeat from the jaws of victory in the Challenge Cup semi-final against Raith Rovers, going out on penalties after leading by multiple goals late on.

[50] Dundee started March with a much-needed win away to Cove Rangers to close the gap at the top to two points ahead of a two-week hiatus.

[51] Dundee started their final round of fixtures flatly with a drab goalless affair away to Partick Thistle, which left them seven points behind the league leaders.

[54] The Dee started the month off with a bang, battering bottom side and new Challenge Cup champions Hamilton Academical 7–0, including a hat-trick from midfielder Lyall Cameron.

[57] In front of a packed Gayfield Park the following week, Dundee could only manage a point in a goalless draw with Arbroath which nevertheless put them top of the league on goal difference with a game in hand.

[62] Prior to the title-deciding game, Dundee winger Paul McMullan was nominated for the PFA Scotland Championship Player of the Year after scoring 7 goals and providing 11 assists in the league this season.