Raith Rovers will have to do something they have never managed before if they are to win promotion to the Premiership.
In seven previous attempts, the Stark’s Park club have NEVER prevailed in the play-offs.
On six of those occasions, dating back 17 years, promotion has been at stake.
And, once, the Kirkcaldy outfit suffered the pain of relegation via an end-of-season shoot-out against Brechin in 2017.
As they await the identity of their semi-final opponents, Courier Sport looks at Raith’s record of play-off frustration.
2006/07 First Division play-offs
Semi-finals: Raith Rovers 1-3 Stirling
Raith’s run of play-off agony began with a defeat to Stirling Albion.
John McGlynn had replaced Dundee United-bound Craig Levein in November and took Rovers to third in the table behind champions Morton and Stirling.
After a first-leg stalemate against the Binos, a Brian Fairbairn strike put Raith in front away from home.
But Chris Aitken instantly levelled from the spot before adding a second and Colin Cramb’s 79th-minute third ended Rovers’ dreams of promotion.
2007/08 First Division play-offs
Semi-finals: Raith Rovers 2-4 Airdrie United
McGlynn’s first full season in charge finished with Raith in third place in the third-tier again.
It meant a play-off clash with Airdrie United, who had finished six points ahead in second.
Allan Russell, who would go on to spend a spell as attacking coach with the England national team, bagged a double at Stark’s Park to give the Diamonds a huge advantage.
Bryan Prunty put Airdrie even further in command in the second-leg but a Graham Weir strike gave Rovers hope.
That was dashed when Peter Donnelly added a fourth for the Lanarkshire men in the tie before Weir’s late consolation.
2015/16 Premiership play-offs
Quarter-finals: Raith Rovers 1-2 Hibernian
With Ray McKinnon at the helm, Raith finished fourth in a Championship won by Rangers.
Taking on third-placed Hibs in the play-offs, they earned the upper hand with a first-leg victory delivered by Harry Panayiotou’s 75th-minute strike against the run of play.
However, early goals from John McGann and Darren McGregor inside the opening 12 minutes turned the tie on its head.
Despite a grandstand finish, Rovers could not find the goal that would have taken the encounter into extra-time.
2016/17 Championship play-offs
Semi-finals: Raith Rovers 4-4 Brechin City (lost 4-3 on penalties)
A disastrous campaign reached a calamitous climax as Raith were relegated to League One, where they would spend three years.
Gary Locke was replaced by John Hughes in the dugout in the February following a horrendous run of 14 games without a win.
And, despite a last-day 2-1 win over Ayr United, the Kirkcaldy outfit ended the season in ninth thanks to a worse goal difference than both Dumbarton and St Mirren.
Declan McManus cancelled out Ross Caldwell’s penalty in the first-leg away to Brechin City.
But they were forced to come from behind twice in the return as Jean-Yves M’voto levelled following Caldwell’s second-half opener and then McManus struck in the 90th minute after Alan Trouten’s strike just six minutes from full-time.
Rovers finally went in front in the tie courtesy of Ryan Hardie in the 13th minute of extra-time but Liam Watt forced penalties with a stunning free-kick leveller five minutes from the end.
Experienced goalkeeper Graeme Smith was Brechin’s hero with three spot-kick saves and Hughes and assistant Kevin McBride left shortly after full-time.
2017/18: Championship play-offs
Semi-finals: Raith Rovers 1-4 Alloa Athletic
With Barry Smith at the helm, Raith finished second after being leapfrogged on the final day by champions Ayr United following a costly goalless draw at home to Alloa.
Alloa were the opponents again in the play-offs and, once more, it was to end in bitter disappointment for Rovers.
A 2-0 defeat away from home in the first-leg did the damage as goals from future Scotland striker Ross Stewart and Iain Flannigan were compounded by Iain Davidson’s late red card.
Alloa stretched their lead in the tie with Jordan Kirkpatrick’s breakthrough in the second-leg at Stark’s Park.
And Euan Murray’s strike shortly after half-time could not spark a comeback as Stewart sealed victory for the Wasps on the day and in the tie.
2018/19 Championship play-offs
Semi-finals: Raith Rovers 3-2 Forfar Athletic
Final: Raith Rovers 1-3 Queen of the South
McGlynn returned to Raith as manager in September 2018 but could only lead the team to third in League One behind champions Arbroath and Forfar in second.
They got the better of the latter in the play-offs, however, with goals from Kevin Nisbet and Jamie Gullan, either side of one from former Rovers hero John Baird, earning a 2-1 advantage in the first-leg.
Baird levelled things up in the tie in the return at Station Park. But Michael Travis was red-carded for a last-man foul on Nathan Flanagan and current Scotland internationalist Nisbet clinched the tie from the spot.
Things did not go according to plan in the final, however, as early goals from Lyndon Dykes – another future Scotland star – and Connor Murray, and an own goal from Euan Murray, earned Queen of the South a 3-0 lead at Stark’s Park.
Despite David McKay’s late counter, a goalless stalemate at Palmerston Park sealed promotion for Queens.
2020/21: Premiership play-offs
Quarter-finals: Raith Rovers 2-0 Dunfermline
Semi-finals: Raith Rovers 1-3 Dundee
Following a goalless first-leg at East End Park, third-placed Raith prevailed in the quarter-finals against Dunfermline with a 2-0 victory on home soil.
The Pars had the better of the early chances. But Lewis Vaughan brilliantly broke the deadlock when he lifted a loose ball over the grounded Owain Fon-Williams before scoring from close range.
With Gozie Ugwu adding a late second for McGlynn’s men, it was on to a meeting with Dundee, who had finished second in the table behind champions Hearts.
Charlie Adam was the Dark Blues’ inspiration in a 3-0 victory at Stark’s Park, setting up Jordan McGhee for a double before Osman Sow added a late third.
Vaughan gave Rovers hope in the second-leg at Dens Park with a 21st-minute opener. But, despite chances, they could not get another to put on further pressure.
