Tottenham Hotspur are underdogs for Sunday’s League Cup final against Manchester City, but a Spurs win would not be as big a surprise as the following upsets…

Bradford City vs Arsenal, 2012

Bradford enjoyed a historic run to the League Cup final in 2012/13, famously beating Premier League side Aston Villa over two legs in the semi-finals. The fourth-tier outfit may have been thrashed 5-0 by Swansea City in the Wembley showpiece, but their fourth-round victory over Arsenal will live long in the memories of all those who witnessed it at Valley Parade.

Garry Thompson gave the Bantams an unlikely lead after the quarter-hour mark, but Thomas Vermaelen’s late header spared Arsenal’s blushes – for a few more minutes, at least. It was the Belgian defender who missed the decisive penalty in the shoot-out, as goals from Nathan Doyle, Gary Jones and Alan Connell sent Bradford into dreamland.

Grimsby Town vs Tottenham, 2005

If Tottenham beat Chelsea and reach the final of this year’s competition, they will have done it the hard way by overcoming four Premier League sides. They were handed an easier draw in 2005/06 but failed to take advantage, losing 1-0 to Grimsby in the second round.

The League Two team had shocked Derby County a few weeks previously, but a Spurs side featuring Robbie Keane, Ledley King, Jermain Defoe and Michael Carrick were expected to be far too strong. Yet the Mariners defended valiantly and then found the net in the 89th minute, as Kamudimba Kalala found the net from 20 yards to send Martin Jol’s charges out.

Milton Keynes Dons vs Manchester United, 2014

Louis van Gaal got his Manchester United tenure off to a miserable start, losing 2-1 to Swansea on the opening day of the Premier League season in 2014/15. Things somehow got even worse a few days later, as the Red Devils suffered a humiliating 4-0 defeat by MK Dons of League One.

Will Grigg and Benik Afobe both notched braces for Karl Robinson’s side, who also included a young Dele Alli among their number. Van Gaal had rotated his own team for this midweek clash, but a starting XI containing David de Gea, Danny Welbeck and Shinji Kagawa should still have done a lot better.

Liverpool vs Northampton Town, 2010

There were few bright spots during Roy Hodgson’s ill-fated spell as Liverpool manager, but this was arguably the nadir. Milan Jovanovic put the Reds in front early on at Anfield, but Billy McKay’s second-half strike was enough for Northampton to force extra time.

The League Two strugglers then edged ahead through Michael Jacobs, and although David Ngog made it 2-2 with four minutes left on the clock, Town held their nerve to triumph on penalties after Nathan Eccleston struck the bar with Liverpool’s fourth attempt.

Southend United vs Manchester United, 2006

Wayne Rooney and Cristiano Ronaldo were among those who started Manchester United’s fourth-round meeting with Southend in 2006/07, but the presence of the two forwards was not enough for Alex Ferguson’s side to avoid a shock loss at Roots Hall.

The Shrimpers, who would go on to be relegated from the Championship in May, had beaten Bournemouth, Brighton and Hove Albion and Leeds United in previous rounds, but their luck was expected to run out against the Red Devils. Instead, Freddy Eastwood’s brilliant free-kick was enough for the south coast side to record perhaps the greatest result in their history.