[1] Due to the disruption caused by the COVID-19 pandemic, the teams in the Scottish Championship agreed to shorten the season to 27 games rather than the regular 36, with a start date on 17 October 2020.

[7][8] After discussions lasting several weeks, 12 of the 13 players asked to take cuts agreed, with striker Kane Hemmings the only one to hold out longer.

[19] The Dark Blues looked set to repeat this result the following week against newly-promoted Raith Rovers through Charlie Adam's strike, but a late equaliser denied them from taking another 3 points.

[20] Dundee would again struggle away from home, needing inspiration from Adam to score two late goals against part-time Alloa Athletic in order to escape Recreation Park with a point in a wild 3–3 draw.

[23] Despite equalling high-flying Premiership side Hibernian for most of their final group stage game, a late flurry from the Hibees would result in a heavy 4–1 defeat, though Dundee would still qualify for the following round of the cup.

[27] In their first home league game in over a month, Dundee would return to winning ways with another tight 1–0 victory against Arbroath through a Paul McGowan solo goal.

[29] Dundee looked to have swept past high-flying league rivals Dunfermline Athletic with a dominant 3–0 lead late on, but a quick collapse allowed the Pars to snatch an unlikely point at Dens Park.

[30] Despite the prior week's disappointment, the side put it aside and would record a comfortable Boxing Day win away to Queen of the South through an Osman Sow hat-trick.

[32] Dundee would gain a measure of revenge over their opening day humiliation against Hearts with a commanding 3–1 win at Dens, scoring 3 goals in 4 consecutive games for the first time since January 1978, exactly 43 years prior.

A combination of Dens Park's pitch issues and heavy snow brought on by Storm Darcy worked to postpone several games for Dundee throughout February.

[43] Dundee would get consecutive wins in dramatic fashion the following week, coming back from an early 0–2 deficit to defeat play-off rivals Dunfermline Athletic.

[49] The Dees would however get an important victory at Dens against Raith Rovers to ensure their place in the Premiership play-offs and give them one last chance at finishing in 2nd.

[50] In the final game of the league campaign, a comfortable win courtesy of a Jason Cummings brace and a defeat for Raith allowed Dundee to sneak into 2nd place.