Relegated and falling at the final hurdle the next season – it wasn’t the way Sean Dillon wanted to leave Dundee United after 10 years’ service.
A 2010 Scottish Cup winner with 346 appearances in tangerine under his belt, Dillon is something of a club legend.
However, his exit hurt the Irishman. United’s failed play-off attempt in 2017 stung as much as the drop the year before as the defender left Tannadice for Montrose that summer.
Dillon wishes it was different but admits he is delighted the current crop have hauled the club back into the Premiership under old pal Robbie Neilson.
“There was a lot of hurt. It was brutal,” the 36-year-old says of their relegation and botched promotion push.
“Despite how good things were going you’ve got it in your head until the last ‘we’ve got to do this’.
“When it doesn’t happen it’s a tough one to take, especially with me leaving not long after.
“It wasn’t a great time, unfortunately.
“It’s like any team – there’s nothing worse than when that happens.
“It was, obviously, devastating from a personal point of view but more so for the fans and everybody involved at the club.
“It was the last thing I wanted to do at the end of my time at the club. That’s selfish talk but the biggest thing was it was horrible for the fans.
“The fact that Robbie’s done the job is great. I played with Robbie and I’ve a lot of time for him.
“I’m absolutely delighted for him and I know a couple of the boys in the squad at moment and it’s brilliant for them.
“I’m really pleased for everybody involved in the club – Paul Reid, Joe Rice and everybody who has been there for so long.
“It’s not been easy. They’ve had a lot to put up with, with everything that’s gone on.
“It’s much better for those guys to be doing their job in the Premiership and have big games to look forward to.”
For Dillon, a guest on the latest instalment of the Evening Telegraph’s Twa Teams, One Street podcast, things appear better on and off the pitch at Tannadice these days.
And he hopes Neilson’s men can push on in the top flight next season.
“Everything about the club seems better,” he continues.
“I had a great time when I was there but it was heart-breaking the way it went.
“Not to be part of the team which actually got them promoted, when you’re in a positon where you go into the Championship and want to get out of it, hurts.
“It didn’t work for us and it’s a tough one to take.
“When you play a role in the club getting relegated the biggest thing you want to do is be part of it coming back up.
“It wasn’t to be for me but I’m buzzing for the boys that have done it.”
Of the Tangerines’ top-six, silverware and European ambitions, Dillon adds: “What they’ve achieved already is brilliant.
“It’s great to see them back to where I believe they should be.
“I definitely think they can get back in there. I’m not going to say I would expect it but I certainly wouldn’t be surprised if they go on and do really well.
“Robbie’s done a great job already and I’d love to see them continuing on.”
Dillon insists the most important aspect is the fans have hope moving into the future that the glory days will return.
He continues: “You want to see your former clubs doing well, you always look out for teams or players you’ve played with.
“Robbie and United come into that category but, ultimately, the biggest buzz for me will be for the fans.
“You see the crowds they’ve had this year and the travelling supports – they’ve been absolutely brilliant.
“It’s a reward for constantly being there and taking such big crowds around the country.
“You take it for granted sometimes the fact the club has done so well for so long.
“You get into that frame of mind that ‘we’re a Premiership club’ and you’re fighting for European football.
“When you do it over a period of time it becomes the norm and that’s a great thing to be involved in.
“But when it doesn’t happen and things change you need to roll with that.
“The fact they’re back up as soon as possible is the first step and I’m delighted for them.
“It’s a shame they didn’t get to celebrate the way they would’ve wanted but it’s job done that’s the main thing.”