The final was still to come and, while it was disappointing to lose to Celtic, the positive impact of that cup run had already been felt.
“For a club in our situation it was a financial windfall because it hadn’t been budgeted for so it helped us for around three years. The feeling of relief was amazing and I wouldn’t mind that feeling again on Sunday.”
This time, in her role at Hibernian, the relief would not be fuelled by the kind of monetary woes which kept her awake at night during her spell at the helm at Fir Park but by the desire to reward the Hibs fans who have had to withstand disappointment and barbs in recent years but who have still stuck by the club.
“It hasn’t been easy for them,” said the Hibernian chief executive, who has spent her tenure in Leith actively trying to re-engage with disillusioned supporters and reignite a sense of togetherness under every department of the club and the fanbase.
“There’s been disappointments around cups, as we know, and there’s been relegation, but supporters have turned out even at the hardest times. There were 5,500 season tickets sold when I came in but by the time we started in the Championship last season it was 7,500 and, while that might not seem much to some people, to me it is a significant amount. That’s a whole bunch of people who could have said ‘I’m not going on this journey’ but they didn’t so I would like to be successful for them.”
There are some clubs where glory days punctuate their history but, for the majority, cup finals are hard to come by, cup triumphs even more elusive. Thus far, the Easter Road side have secured Sunday’s trip to Hampden for the League Cup final and they are still in the reckoning for another shot at the Scottish Cup. Winning either will not be easy, says Dempster, who is an admirer of fellow League Cup finalists Ross County.
“But I would absolutely love it and, of course, my family are going to be there as well so that would be great for me if I could celebrate with them.”
Growing up in the west of Scotland, with two brothers, they would sit around the table talking football with their dad and she believes it is hard to live in this country and not be a football fan. It always ends up being part of your life, she says, even if it is a vicarious association, a point proven by her mother, who, despite being more interested in bingo, still takes notice of the results and fixtures which now play such a key role in whether her daughter can enjoy reading the morning papers or not.
But Dempster was originally brought into Motherwell by then owner John Boyle because she did not have any direct experience of running a football club or traversing the tricky minefield of imbedded views when it came to the administration of the game.
“I’m sometimes flippant about it and say he just wanted to throw me in there to see what would happen but, coming in cold, he knew that I would help shake things up because I would ask a lot of questions. I have never been scared of saying ‘I don’t understand that’ or pulling things apart.”
With a background of more than 20 years in media and advertising, which she describes as an “empowering environment”, she developed the thick skin needed to survive in football and learned about taking responsibility, understanding the demographics of the customers and fine-tuned her debating skills. Boyle had spotted her potential during their numerous meetings on several of his business accounts. “There was always a tension between us because, when you work in media and have a client, often you are trying to tell them what to do and listening was never his forte! But because I was quite challenging I think that appealed to him.”
As he hoped, Dempster has proved a breath of fresh air in many regards since she entered the footballing fray in 2008 and, having known little, she learned fast. But it has been challenging and still is.
The loss of the Setanta television money not long after she had joined Motherwell helped focus people’s minds, she says, but Scottish football is still feeling its way. She envisages some necessary changes in the SPFL board in the summer but predicts a period of greater contemplation and positivity as clubs use the period between now and the new TV deal in 2020 to sketch out a more sustainable way forward for the game in this country.
“To say that the economics of the game in Scotland are challenging would be underplaying it but it does feel that it is tilting in the right direction.
“I think what you are seeing now is the results of Setanta, financial difficulties, even administration for some clubs, all the well documented issues of the last four or five years that meant that football had to look in on itself. I think we went through periods of being quite destructive in a way, often unintentionally, but I think more people are working better in partnership.”
She showed strength of character when voting for a more equal share of the pot between clubs, which hampered Motherwell who finished second that season and would have benefited short-term from the disparity. “But we had always been a club who said that differential was too big and for us not to support that would have been a double standard and smacked of opportunism.”
Which is why she is not in favour of league reconstruction now, even if it would provide Hibs with a more stress-free route back to the top table. “Of course there is a temptation to say yes but, if you are holding true to what is better for the game, I think what we have just now is working well. We all just need to work together in a smarter way to bring people back to football.”
A side with momentum and pushing for automatic promotion a couple of weeks ago, a short burst of untimely defeats has killed off that hope but Dempster says the target of making it back to the Premiership can still be achieved via the play-offs. “There are no wheels coming off,” she says defiantly. And, if they don’t make it up this year, there will be no let up in the ambition.
“We lost around £800,000 last year and we are on target to be somewhere near that again but we have not done the work we have done in the past two years to rebuild the structure within this great club to just chuck it if the worst happens. You have to be bold.
“I’m not thinking about it just now because I don’t want it creeping into anyone’s psyche but the foot will not be coming off the pedal. There are expectations at this club and we need to fulfil those.”