Steven Pressley Transforms Dundee's Fortunes After Derby Win

Steven Pressley cut an almost carefree figure as he strode down Tannadice Street, tote bag slung over his shoulder, grin fixed in place. It was a short walk to one of the longest, most unforgiving fixtures in his career – the Dundee derby.

Twelve months earlier, that same walk felt very different.

Back then, the new Dundee boss was still battling open hostility from a support furious at his appointment. A miserable League Cup exit, courtesy of back-to-back defeats to lower-league sides, did nothing to ease the tension. Nor did a five-game winless start to the Premiership season.

The fourth of those matches was a 2-0 home defeat to Dundee United. The kind of result that turns grumbling into full-blown revolt. Pressley, 52 and under siege, looked like a short-term experiment.

Fast forward a year and the scoreboard reads the same – 2-0 – but the names are flipped. This time it is Dundee celebrating, Pressley’s team marching off at Tannadice with the away end roaring and their side sitting second in the table.

“I’m immensely proud of this group of players,” he told BBC Scotland, the noise of the derby still ringing in his ears. “Derby games are never won on tactical detail, they’re won on spirit and determination and I think we had that in abundance.”

It is classic Pressley: calm, direct, and unwilling to pretend everything went exactly to plan.

Because, as he admitted, it didn’t.

“We didn’t carry out any part of [the game plan] to be honest,” he said. “But what was very apparent in our performance was the grit and determination that your supporters are generally so proud of.”

That grit has been building for a while. Stretch the form line back to the end of last season and a pattern emerges. Dundee survived thanks to three wins in their final four league games. Add in this campaign’s start and Pressley’s side have now taken five victories from their past seven Premiership matches.

It is not a fluke. It is a team that has learned how to suffer and still come out swinging.

Pressley will not shout about targets in public. He remains measured, wary of getting carried away by a strong August. But inside the dressing room, there is no doubt: Dundee want more than last season’s eighth place.

“What’s most pleasing is that the three league games have been incredibly difficult games,” he said. “But there’s a spirit and togetherness about us just now that is serving us well.”

A year ago, plenty viewed him as a punchline. The former Carlisle United manager, parachuted into Dens Park, mocked before he’d even taken a training session. That perception has been quietly dismantled.

His personality helps. Players talk about his honesty, his humour, the way he backs them when others don’t. But behind the charm is a coach sharpened by four years at Brentford, one of the Premier League’s most admired operations. The work done there is written all over this Dundee squad.

Pressley has leaned on his contacts south of the border to pull off smart loan deals, but this is not a team of stars. It is a side stitched together from Scottish football’s overlooked and underused.

Ryan Flynn, now at Arbroath and once under Pressley at Falkirk, described him to BBC Scotland as a master at instilling confidence and creating an environment where players believe they can thrive. The evidence is in the line-up.

Drey Wright, who opened the scoring in the derby, has turned into a key figure since arriving from St Johnstone, his versatility and running power giving Dundee a constant outlet. Alan Forrest, discarded by Hearts, has found a new platform. Forwards Charlie Reilly and Joe Bevan were plying their trade with Albion Rovers not so long ago.

Then there is Owen Bevan. On loan at Hibernian in 2024 and unable to force a single appearance, the centre-back stepped into the heat of Tannadice and shone. He grabbed the second goal, but his partnership with Ryan Astley at the back – especially during United’s best spells – underpinned the win.

They bent at times. They did not break.

“Sometimes winning away from home is being comfortable with the uncomfortable and we did that at times,” Pressley said.

He refused to dress it up as some tactical masterclass.

“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.”

From a joke figure to the architect of a side sitting second in the Premiership, Pressley walked back up Tannadice Street very differently from the way he arrived last year. The question now is not whether he belongs at Dundee – it is how far this unlikely, patched-together group can push the rest of the division.