Four Scottish clubs go in search of a £5million Conference League bounty this week. For Rangers, it might seem like the ultimate consolation prize. They have spent multiples of that on players who have struggled to prove they belong even at that level. But for Hearts, Hibs and Motherwell, that prize pot is gold.
Historic play-off pain
They are going to have to dig deeper than any non-Old Firm side before them to land the riches. Incredibly, history will tell you that no Scottish side outside of Celtic and Rangers has ever won a tie at this stage. It has been a 17-year tale of play-off pain.
The system was introduced to the Europa League in 2009 then the Conference League in 2021, and apart from Glasgow's big two, there have been 16 attempts made by Scottish sides to cross the threshold into the money-spinning group stage or league phase. Every one of those attempts has ended in defeat.
Hearts, Hibs and Motherwell's attempts
When Hearts and Aberdeen have played group stage football it has been as a result of dropping out of the competition above. For Hearts, Wednesday's tie against Rapid Vienna will be their seventh attempt at a play-off, having lost to Dinamo Zagreb in 2009, Spurs in 2011, Liverpool the following year, Zurich in 2022, PAOK in 2023 and Viktoria Plzen two years ago.
Hibs were left heartbroken at this stage a year ago when an injury-time Legia Warsaw goal in Poland took the tie to extra time before David Gray's side bowed out. The Easter Road side also lost heavily to Aston Villa, 8-0 on aggregate, three years ago in their only other previous play-off tie. Motherwell are also contesting their third play-off, having lost to La Liga side Levante in 2012 and Odense in 2010.
Other Scottish disappointments
Elsewhere, the Scottish tale of woe has seen St Johnstone lose to Austrians LASK at this stage of the very first Conference League competition in 2021, likewise Kilmarnock were beaten by Copenhagen in 2024, while Dundee United's only play-off appearance ended in a narrow 2-1 defeat to AEK Athens in 2010. Aberdeen have also lost all three of the play-offs they have been involved in, against FCSB, BK Hacken and Qarabag.
It is a pitiful record. But it can change over the next two days. Motherwell might be right up against it in their tie with Europa League runners-up Freiburg after the Germans' 3-1 first leg win at Fir Park. But Hearts and Hibs have a proper fighting chance.
Chance to break the curse
The Jambos may be underdogs away to Rapid, with the tie sitting finely poised at 2-2 from the first leg. But with each passing week, Wouter Vrancken's side are looking better and stronger. They have players who can hurt the best of teams at the top end of the pitch. They are scoring goals for fun and sharing the load too.
It is all about finding a way to close the door in their own end against an equally expansive side that is sitting top of the Austrian Bundesliga for a reason. Do that in the Allianz Stadion on Wednesday night and the Gorgie men have a real chance of hitting the jackpot.
Across Edinburgh, Hibs maybe have the best opportunity of them all. David Gray's side are staring at a one-off shot at not just a £5m windfall but a place in the history books to go with it. No Hibs side has ever qualified for group stage football since the European competitions were given a shake-up two decades ago.
But with home advantage against Belgians Gent and with the scoreline at 0-0 from the first leg, the odds might be sliding in the Hibees' favour. They produced some huge performances last season against Midtjylland, Partizan Belgrade and Legia Warsaw. A similar display on Thursday night - with match winners like Martin Boyle and Owen Elding stepping up to the plate - will give Gray's men a fantastic chance at making history. Scottish football needs these capital gains as much as the Edinburgh duo. It is time to blow apart that play-off curse.
