Former Dens defender Jim Lauchlan says “it was the biggest disappointment of his career” to miss out on promotion back to the top flight under Jocky Scott.
The former Dundee United man returned to Tannadice Street but on the other side of the road as Alex Rae snapped up the no-nonsense defender in the summer of 2008.
Despite his history with their fierce rivals, Dundee fans took to Lauchlan thanks to his never-say-die attitude and wholehearted approach to life at Dens Park.
Signed after departing Queen of the South as Rae plotted promotion from the First Division, injury saw Lauchlan restricted to the sidelines early on.
A slow start, however, saw a change in manager as club legend Jocky returned for his third stint.
The following season, the Dens men missed out on promotion as they finished second to Inverness.
Lauchlan said: “I signed for Alex Rae after a pre-season tour in Malta but it never started well when the season began.
“I got injured and it was really frustrating.
“I just wasn’t able to play for Alex before he lost his job.
“Then came in Jocky Scott and he was first class and I had huge respect for him. We were backed and he brought in Leigh Griffiths and Gary Harkins and we had a fantastic team that season.
“We won the Challenge Cup, my first medal, after coming from 2-0 down against Inverness at McDiarmid Park.
“For me, it was the biggest disappointment of my career that we didn’t do it that season.
“We had the backing from the fans as well and it was such a shame we didn’t manage to get over the line.”
With Inverness speeding to the title, the board at Dens decided it was time for another change in manager. Jocky was sacked in March – a move Lauchlan thought was a wrong one.
He added: “Jocky lost his job and it was a surprise to me a the time – I think the club panicked a wee bit.
“He was, obviously, a Dundee man through and through, the fans were behind him and we had the squad to do it. The timing was strange, too, and I think it affected the squad.”
Read more from the Millennium Managers series here.
Lauchlan revealed he looks back on his time at the club with real fondness. However, his departure left a “bitter taste”.
“Gordon Chisholm came in. He had already let me go at Queens and I thought ‘here we go again’.
“By the end, I got in his team and ended up captaining Dundee a few times but then he let me go.
“I was hugely disappointed because I’d played well for him and it left a bitter taste. I was Player of the Year in 2010 and had a good rapport with the fans.
“I had won loads of Player of the Year trophies on the Sunday, could barely fit them in my car, and then on the Monday was brought in and told I was getting released.
“I actually asked him how many players had been Player of the Year and got released at the end of it.”
He added: “I loved it at Dundee and I gave all I could when I played for them.”