Widely dismissed as a figure of fun at this point last year, former Carlisle manager Pressley has won over his squad with a warm personality that makes players eager to work with him.
However, his likeable character should not overshadow his coaching ability, which has evidently improved throughout four years with flourishing Premier League side Brentford.
Pressley’s connections in England have allowed Dundee to secure some excellent loan signings over the past year, although much of the squad has been assembled from players overlooked elsewhere in Scottish football.
Arbroath midfielder Ryan Flynn, who played under Pressley at Falkirk, described his former manager as highly skilled at building players’ confidence and creating an encouraging atmosphere in which they can thrive.
Drey Wright, a versatile player who opened the scoring in Saturday’s derby, has established himself as an important member of the squad since arriving from St Johnstone.
Dundee recruited Alan Forrest after Hearts let him go, while fellow attackers Charlie Reilly and Joe Bevan were playing for Albion Rovers just a few years earlier.
Owen Bevan, who scored the second goal, spent time on loan at Hibernian in 2024 without making a senior appearance. The central defender produced an outstanding display alongside Ryan Astley as Dundee endured difficult spells on their way to an impressive derby victory.
Pressley said that earning victories on the road sometimes requires a team to accept uncomfortable situations, something his players managed successfully during parts of the match.
He added that tactical details did not decide the contest; instead, the result came from a group fiercely determined to avoid defeat in the derby, leaving him immensely proud of their effort.
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