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Viewed as a joke figure by many this time last year, former Carlisle boss Pressley's endearing personality is a big reason why players seem to enjoy playing under him.
But that should not detract from his on-field coaching, which has clearly developed during four years at thriving Premier League club Brentford.
Pressley's south-of-the-border contacts have helped Dundee work magic in the loan market over the past year, but much of the team is made of odds and ends from Scottish football.
Arbroath midfielder Ryan Flynn, who worked with Pressley at Falkirk, told BBC Scotland that his former boss is a master at instilling confidence in players and nurturing a positive environment for them to excel in.
Versatile Drey Wright, scorer of the derby opener on Saturday, has become a valuable part of the team since joining from St Johnstone.
Alan Forrest has been picked up after being discarded by Hearts, while fellow forwards Charlie Reilly and Joe Bevan were Albion Rovers players only a few years ago.
Second goalscorer Owen Bevan was on loan at Hibernian in 2024 but failed to make an appearance. The centre-back was fantastic alongside Ryan Astley during periods of suffering 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."
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