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Leicester City’s Most Painful Matches Of The Last 25 Years

Wednesday’s match was awful, but where does it rank?

Leicester City v West Bromwich Albion - Premier League - King Power Stadium Photo by Tim Keeton/PA Images via Getty Images

If you started following Leicester City in the heady days of the 2015/16 season, good for you! However, you may not have been exposed to the full Leicester City experience by joining in when you did. The last five years have been the most successful in the history of the club. Ours is a club that has known disappointment, discouragement, and oh-so-much pain. With that in mind (well, that and Wednesday’s match), I am going to try to determine the most painful match in the club’s last quarter-century.

With that said, as good as the last five years have been, expectations have been raised, and those expectations have given rise to that vilest of emotions: Hope. Fear is not the mind-killer, hope is. This is a long-ish way of saying there will be quite a few recent matches on this list. With dashed hopes comes pain, and that is what we’re looking for.

Yes, I am very much “in a mood” after Wednesday’s match, thank you for asking. Let’s go through the nominees in chronological order:

Tottenham Hotspur 1 - 0 Leicester City (21 March, 1999)

Leicester would reach the League Cup final in 1997, 1999, and 2000, winning it twice. It could, and probably should, have been three. The Foxes squared off against Spurs in the 1999 final. The two sides cancelled each other out for the first hour, but City got a huge boost on the hour. Spurs midfielder Justin Edinburgh waved his arms wildly to protest a Robbie Savage challenge and Savage took full advantage, dropping to floor like he’d been shot and clutching his face. It was a shameful dive, but it worked, and Edinburgh was sent off.

Soccer - Worthington Cup - Final - Leicester City v Tottenham Hotspur
I absolutely could not avoid posting this image. Sorry, Jack.
Photo by Matthew Ashton/EMPICS via Getty Images

The Foxes couldn’t turn their numerical advantage into a goal as future Leicester keeper Ian Walker was imperious in goal. Justice of a sort was done as Allan Nielsen scored in extra time for from a diving header. The fact that Savage had cheated to reduce Spurs to ten men would have taken a little of the shine off a win, but it didn’t make losing to a 10-man side in a cup final feel any better.

Wolverhampton Wanderers 4 - 3 Leicester City (25 October, 2003)

This was certainly one of the least-important matches on this list, but that made it no less painful. Sir Les Ferdinand was in fine form for the Foxes, scoring twice in the first half and setting up Riccardo Scimeca for a third goal for the visitors. Up 3-0 at the half, it looked for all the world as though it would be a Wallacean “Grand Day Out.”

Marcus Bent of Leicester holds off Lee Naylor of Wolves
I’m no expert, but it sure looks like Marcus Bent is gonna be sore tomorrow.
Photo by Tom Shaw/Getty Images

It took only 15 minutes for the lead to evaporate. Wolves were on level terms on the hour and looked very much the more likely side to score again. The Leicester defense tightened up and appeared to have weathered the storm, but Henri Camara scored from six yards out in the 86th minutes to complete the comeback, or, from a Leicester standpoint, the collapse.

Stoke City 0 - 0 Leicester City (4 May, 2008)

It wasn’t a defeat. It was so much worse than that. Coming in to the match, Stoke needed at least a draw to earn promotion to the Premier League and Leicester needed to match Southampton’s result to avoid relegation. Things got off to a good start on the south coast as Sheffield United took an early 1-0 lead over Nigel Pearson’s Southampton. Would we escape the drop?

Images From The Book “In The Moment’ - By Tom Jenkins
Stoke fans invading the pitch after a 0-0 draw is very “on brand.”

No, we would not. A Stern John brace gave the Saints a 3-2 win, meaning the Foxes needed to find a way to win. They poured forward in the last half-hour, going close time and again. Iain Hume and Richard Stearman both went oh-so-close, but the ball would never ripple the back of the net. The match ended in a draw, and Leicester were doomed to spend the following year in the third tier.

Watford 3 - 1 Leicester City, 3 -2 on aggregate (27 May, 2013)

You know this one, or you should. It was the second leg of the League Championship promotion semi-final. City carried a slim 1-0 lead from the first leg at the Walker’s. David Nugent scored for the Foxes but a Matej Vydra brace left the tie level going into injury time. With no away goal rule, extra time beckoned.

Never forget.

It was not to be. Anthony Knockaert won a very, very soft penalty to give us all dreams of Wembley. He took the spot kick, saw it saved. His second effort was collected by the keeper. The Hornets poured down the right side of the pitch, where Fernando Forestieri crossed the ball in to Jonathan Hogg at the far post. The midfielder headed down for Troy Deeney to smash home from close range, turning what looked to have been a Leicester win into a defeat in the blink of an eye.

Bournemouth 4 - 1 Leicester City (12 July, 2020)

You could list any one of several matches following the summer return of football after the COVID-19 pause, but this was the one that really set the tone. The Foxes were still in the driver’s seat to win a spot in the Champion’s League even after this match, but you could feel it slipping away. Did I mention that Bournemouth were relegated and had nothing to play for?

AFC Bournemouth v Leicester City - Premier League
A picture is worth a thousand words, not that I’m going to let that slow me down...
Photo by Glyn Kirk/Pool via Getty Images

Leicester took an early lead through a Vardy tap-in and proceeded to dominate the first hour of the match without adding to the scoreline. Disaster struck when Schmeichel cannoned a goal kick directly off of nearby Wilfred Ndidi. The rebound fell to Callum Wilson, who won a penalty off of Ndidi and leveling the score. Bournemouth scored 3 more comical goals, Cags got sent off, and our swagger was gone.

Leicester City 2 - 4 Tottenham Hotspur (23 May, 2021)

A second successive season with Champions League football on the line on the last day of the season, and a second successive failure. This one really stung because Leicester led twice and held a 2-1 advantage with 15 minutes to play. Not exactly “in the bag”, but surely we could hold on for 15 minutes, right?

Leicester City v Tottenham Hotspur - Premier League
Simply including a picture of Gareth Bale guarantees double the hits on social media.
Photo by Shaun Botterill/Getty Images

Not so much.

Kasper Schmeichel came for a Son cross and missed badly, seeing the ball bounce off his fist and into the net. Gareth Bale got a late brace as the City discipline just completely collapsed. 15 minutes from the Champions League, but it might as well have been a million miles.

Leicester City 2 - 3 Tottenham Hotspur (19 January, 2022)

The Champions League wasn’t on the line, but if you think failing to hold a lead for 15 minutes is bad, how about 12 seconds? In spite of being thoroughly outplayed by the visitors for the majority of the match, City held a 2-1 until the final minute of five minutes of time added on.

The whole collapse only took 80 seconds. Spurs scored with just 12 seconds remaining. Leicester gave the ball away from the ensuing kickoff and Spurs scored again. Both goals were scored by Steven Bergwijn, who should have been sent off right before the deluge, and there were...suspicions...of handball on his first. Sure, the referee was shambolic, but we matched him error for error.


Each and every one of these ruined one or more days for me. Some made me angry. Some just left me staring in disbelief. I know which one hurt me the most, but I’m eager to hear your opinion. What was the most painful Leicester City match of the last 25 years for you? I’ll share my rankings after the poll:


What Was The Most Painful Match For Leicester City of the last 25 years?

This poll is closed

  • 4%
    League Cup Final vs. Spurs (21 March, 1999)
    (5 votes)
  • 0%
    Wolves come back from 3 down to win 4-3 (25 October, 2003)
    (1 vote)
  • 14%
    Draw against Stoke ensuring relegation to the third tier (4 May, 2008)
    (15 votes)
  • 50%
    Playoff semi-final against Watford (27 May, 2013)
    (53 votes)
  • 1%
    Loss to relegated Bournemouth at the end of 2020 (12 July, 2020)
    (2 votes)
  • 14%
    Loss to Spurs at the end of 2021 (23 May, 2021)
    (15 votes)
  • 11%
    Loss to Spurs after leading 2-1 with 12 seconds left in extra-time (19 January, 2022)
    (12 votes)
  • 0%
    Other (please let us know in the comments)
    (1 vote)
104 votes total Vote Now

My ranking:

  1. Watford 2013
  2. Spurs 2021
  3. Stoke 2008
  4. Bournemouth 2020
  5. Spurs 2022
  6. Spurs 1999
  7. Wolves 2003