Middlesbrough could become the first team outside of the Premier League to reach the EFL Cup final in 11 years – if they advance past Chelsea in their semi-final second leg on Tuesday.
The Championship side, playing in their first EFL Cup semi-final since 2004, hold a narrow 1-0 lead going into the second leg at Stamford Bridge.
And Boro are a team with second-tier League Cup final history, having reached the final of the competition while in the First Division back in 1998.
Since 1991, the last time a non-Premier League side lifted the competition, Middlesbrough and six other clubs have reached the final.
So who are the magnificent seven?
Swansea City 5-0 Bradford City (League Two) – 2013
Bradford City had a fairytale run to the Capital One Cup final back in 2013 all while battling for promotion in League Two.
The Bantams beat Premier League Wigan and Arsenal on penalties in the early rounds before defeating top-flight Aston Villa – a team ranked 62 places above them – 4-3 over two legs in the semi-finals.
It meant Phil Parkinson’s team reached their first major cup final since 1911 and were the first fourth-tier side to reach the League Cup final since Rochdale in 1962.
They were well beaten by Swansea City, but returned to Wembley three months later to beat Northampton Town 3-0 in the League Two play-off final.
Liverpool 2-2 Cardiff City (Championship), Liverpool won 3-2 on penalties – 2012
Cardiff City put their fans through the mill on the way to the 2012 Carling Cup final.
The Bluebirds won two ties in extra-time and another two on penalties, including their all-Championship semi-final with Crystal Palace.
They took a surprise lead over Kenny Dalgleish’s Liverpool in the final through Joe Mason in the first half, but Martin Skrtel’s leveller forced extra time where Dirk Kuyt turned things around for the Reds.
Ben Turner equalised for Cardiff with two minutes of extra time remaining and the underdogs led after two penalties each in the shootout.
But Anthony Gerrard – Steven’s cousin – put the decisive spot-kick wide and Malky Mackay’s side ultimately missed out on a first major trophy since 1927.
Birmingham City (First Division) 1-1 Liverpool, Liverpool won 5-4 on penalties – 2001
Championship Birmingham City were narrowly beaten by Liverpool in the first major British cup final at the Millennium Stadium.
Trevor Francis’ Blues had edged out Premier League Tottenham, Newcastle and Ipswich on their way to their match-up with the Reds.
They looked to be sliding to a 1-0 defeat in the Worthington Cup final until Darren Purse’s penalty forced extra time.
In the shootout though Andrew Johnson missed his sudden death spot-kick as Liverpool collected their first of three trophies that season.
And Blues would have further penalty woes that season, losing to Preston North End in the play-off semi-finals, although they would eventually lift the League Cup as a Premier League team 10 years later.
Leicester City 2-1 Tranmere Rovers (First Division) – 2000
First Division side Tranmere Rovers beat Premier League outfits Coventry City and Middlesbrough on their way to their first major final in 116 years.
Powered by the long throw of Dave Challinor, Rovers contributed to a tight Worthington Cup final with Leicester, the competition’s last at the old Wembley.
Tranmere’s David Kelly cancelled out Matt Elliott’s early opener for Leicester in the 77th minute, but the Foxes captain restored his side’s lead four minutes later.
John Aldridge’s team ultimately finished 13th in the First Division and were relegated the following year.
Chelsea 2-0 Middlesbrough (First Division) AET – 1998
This was a repeat of the previous year’s FA Cup final, which Chelsea also won 2-0.
On that occasion, Roberto Di Matteo had scored the opening goal to send the Blues on the way to victory and he was Middlesbrough tormentor again, this time grabbing the second goal to end the First Division side’s hopes of silverware.
It had been a tightly contested match that went to extra time, with Frank Sinclair getting the opening goal before Di Matteo struck.
The game was also notable for Middlesbrough handing a debut to Paul Gascoigne, but he was unable to help cause an upset after coming on in the second half.
Liverpool 2-1 Bolton Wanderers (First Division) – 1995
Bolton, then playing in the old First Division, reached their first EFL Cup final back in 1995 but faced a daunting task against then four-time winners Liverpool.
So it proved as the Reds’ top-flight quality told with a Steve McManaman goal in each half putting them in control.
Alan Thompson got one back for Bolton but it was ultimately a consolation as Liverpool claimed a fifth League Cup.
Bolton would have Wembley joy that season though, winning a thrilling play-off final against Reading 4-3.
Manchester United 0-1 Sheffield Wednesday (Second Division) – 1991
And finally, some non-top flight success.
This one is from just before the Premier League era began but was undoubtedly a shock result as Manchester United – winners of the FA Cup in the previous season – went in as heavy favourites against Sheffield Wednesday of the Second Division.
The Red Devils boasted Bryan Robson, Paul Ince and Mark Hughes in their ranks while Wednesday were playing in their first major cup final for 25 years while also battling to make a return to the top flight.
And it was the second-tier side that secured the memorable win thanks to John Sheridan’s first-half goal.
It remains the last time a team from outside the top flight has won any major trophy.