Once seen by many as a figure of fun this time last year, former Carlisle manager Pressley has won players over with his likeable personality.
That shouldn’t overshadow his work on the training ground, which has clearly progressed during four years at a thriving Premier League Brentford.
His contacts in England have helped Dundee pull off some smart loan deals over the past year, though much of the squad is still a mix of overlooked talents from across Scottish football.
Arbroath midfielder Ryan Flynn, who played under Pressley at Falkirk, told BBC Scotland his old boss is outstanding at building players’ confidence and creating a positive environment for them to flourish.
Versatile Drey Wright, who opened the scoring in Saturday’s derby, has become an important piece since arriving from St Johnstone.
Alan Forrest was picked up after being released by Hearts, while fellow forwards Charlie Reilly and Joe Bevan were with Albion Rovers only a few years ago.
The second goalscorer, Owen Bevan, spent 2024 on loan at Hibernian without making an appearance, yet the centre-back was excellent alongside Ryan Astley as they weathered tough spells in an impressive derby win.
“Sometimes winning away from home is being comfortable with the uncomfortable and we did that at times,” Pressley said.
“It was no tactical detail that won us the game today, it was a group of players that were determined not to lose that derby and I couldn’t be prouder of them.”