WREXHAM, UNITED KINGDOM - JANUARY 04: Wrexham striker Steve Watkin (2nd r) scores the winning goal past David Seaman watched by left to right, David O' Leary, Tony Adams (floor) Gordon Davies and Lee Dixon during the FA Cup 3rd round match between Fourth Division Wrexham and Arsenal at the Racecourse Ground on January 4, 1992 in Wrexham, Wales. (Photo by Stephen Munday/Allsport/Getty Images)
Arsenal’s 5 biggest FA Cup upsets
Arsenal 0-1 Blackburn Rovers (2013)
Arsenal were upset by Championship side Blackburn Rovers in 2013. (Photo by Shaun Botterill/Getty Images)
The Gunners were enduring an eight-year trophy drought when they were beaten 1-0 by Championship side Blackburn Rovers in the 2013 quarter-finals.
The visitors defended superbly to frustrate Arsene Wenger’s Gunners as Gervinho, Tomas Rosicky, and Theo Walcott all came close to either opening the scoring or equalising late on.
Blackburn’s winning moment came with 20 minutes remaining when Colin Kazim-Richards reacted the sharpest to Martin Olsson’s saved effort.
Kazim-Richards’ scuffed rebound went in off the post to give the visitors the lead and despite Wenger throwing on a few of the big guns in the closing stages, Blackburn defended resolutely to preserve their advantage.
Continued on the next slide…
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<p>— Vital Wal$all (@VitalWalsall) <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/VitalWalsall/status/820224753692737536?ref_src=twsrc%5Etfw%22>January 14, 2017</a></p></blockquote>
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<p>Ah yes, the great shock of ’33. I remember it well. For some (Walsall supporters), this is the greatest FA Cup upset of all time.</p>
<p>Herbert Chapman’s revolutionary Arsenal outfit were as mighty as they come, and they were expected to waltz beyond the Saddlers, then competing in the Division Three Northern Section, in this cup tie.</p>
<p>Chapman’s W-M-using Gunners were an immense counter-attacking outfit, but they came unstuck against the minnows in a stunning 2-0 defeat. Gilbert Alsop and Bill Sheppard grabbed second-half goals for Walsall against a rotated Arsenal side.</p>
<p>Tommy Black, who conceded the penalty which led to Walsall’s second goal, was reportedly told by the Chapman on the way home from the defeat to never be seen at Highbury again before he was sold to Plymouth the following week.</p>
<p><em>Continued on the next slide…</em></p>
<div class="next-slide slider"> <a class="next-slide-btn" style="background: #c01f2f" data-track="shortcode" data-track-action="next-slide-shortcode" href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"#"> <span class="title">Next:</span> #2 biggest FA Cup upset </a>
</div><!—pageview_candidate—><hr id="pagebreak"><h2>Wrexham 2-1 Arsenal (1992)</h2>
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<blockquote class="twitter-tweet" data-width="500" data-dnt="true">
<p lang="en" dir="ltr">WELCOME TO WREXHAM PILOT EPISODE 🏴󠁧󠁢󠁷󠁬󠁳󠁿 Long before they were America’s favorite fifth-tier Welsh side, Wrexham pulled off one of the most famous <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/hashtag/FACup?src=hash&ref_src=twsrc%5Etfw%22>#FACup</a> upsets of all-time, beating Arsenal 2-1 back in 1992. <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://t.co/Ng7ADrbHnP">pic.twitter.com/Ng7ADrbHnP
<p>— Men in Blazers (@MenInBlazers) <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/MenInBlazers/status/1611757566518001666?ref_src=twsrc%5Etfw%22>January 7, 2023</a></p></blockquote>
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<p>Before Hollywood joined the party. AFC Wrexham were best remembered as the side that unforgettably dumped Arsenal out of the FA Cup in 1992.</p>
<p>This was a mammoth upset with Wrexham competing in the Fourth Division at the time. Arsenal, meanwhile, were the reigning First Division champions and their starting XI at the Racecourse Ground was littered with stars.</p>
<p>David Seaman, Lee Dixon, Tony Adams, David Rocastle, Kevin Campbell, Alan Smith, and Paul Merson were all named in George Graham’s XI and the visitors took the lead just before half-time through Smith.</p>
<p>The hosts proved to be no pushover, however, and they continued to disrupt the Gunners’ rhythm in the second period before they won a free-kick with eight minutes remaining. Skipper Mickey Thomas stepped up and thumped his effort beyond Seaman before Steve Watkin tapped home the winner just two minutes later.</p>
<p>Graham described the defeat as his “lowest moment in football”, while legendary commentator Jon Motson later labelled Wrexham’s victory as a “giant killing which has stood the test of time.”</p>
<p><em>Continued on the next slide…</em></p>
<div class="next-slide slider"> <a class="next-slide-btn" style="background: #c01f2f" data-track="shortcode" data-track-action="next-slide-shortcode" href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"#"> <span class="title">Next:</span> #3 biggest FA Cup upset </a>
</div><!—pageview_candidate—><hr id="pagebreak"><h2>Arsenal 0-2 Millwall (1995)</h2>
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<p lang="en" dir="ltr"><a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/hashtag/OnThisDay?src=hash&ref_src=twsrc%5Etfw%22>#OnThisDay</a> 18th January 1995</p>
<p>Millwall provided a huge FA Cup upset when they won at London rivals Arsenal. Goals from Mark Beard and Mark Kennedy earned the Lions another all-London clash with Chelsea in round 4. <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/hashtag/Millwall?src=hash&ref_src=twsrc%5Etfw%22>#Millwall</a> <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://t.co/hAHEgp6lfv">pic.twitter.com/hAHEgp6lfv
<p>— Football Memories (@FootballOnThis1) <a href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://twitter.com/FootballOnThis1/status/1483375275140333568?ref_src=twsrc%5Etfw%22>January 18, 2022</a></p></blockquote>
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<p>1994/95 was a pretty miserable season for the Gunners as they finished 12th in the Premier League and were beaten in two European finals.</p>
<p>The darkest moment, however, arrived in the FA Cup third round as Millwall visited Highbury for a replay after the two sides drew 0-0 at The Den.</p>
<p>Arsenal’s season was slowly disintegrating ahead of this cup tie and they’d been dumped out of the League Cup by Liverpool just days before this game.</p>
<p>Their woes worsened when the youthful visitors grabbed an early lead through Mark Beard and never looked like relinquishing their advantage. Graham’s Gunners were out of ideas against the second-tier side and Millwall scored a second to close out the contest in stoppage time.</p>
<p><em>Continued on the next slide…</em></p>
<div class="next-slide slider"> <a class="next-slide-btn" style="background: #c01f2f" data-track="shortcode" data-track-action="next-slide-shortcode" href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"#"> <span class="title">Next:</span> #3 biggest FA Cup upse </a>
</div><!—pageview_candidate—><hr id="pagebreak"><h2>Arsenal 0-1 Blackburn Rovers (2013)</h2>
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<img decoding="async" loading="lazy" class="size-full wp-image-131587" src=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://images2.minutemediacdn.com/image/fetch/c_fill,g_auto,f_auto,h_2129,w_3200/https%3A%2F%2Fpaininthearsenal.com%2Fwp-content%2Fuploads%2Fgetty-images%2F2017%2F07%2F161795145.jpeg" alt="" width="3200" height="2129" srcset="https://paininthearsenal.com/wp-content/uploads/getty-images/2017/07/161795145.jpeg 3200w, https://paininthearsenal.com/wp-content/uploads/getty-images/2017/07/161795145-768x511.jpeg 768w" sizes="(max-width: 3200px) 100vw, 3200px"><p class="wp-caption-text">Arsenal were upset by Championship side Blackburn Rovers in 2013. (Photo by Shaun Botterill/Getty Images)</p>
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<p>The Gunners were enduring an eight-year trophy drought when they were beaten 1-0 by Championship side Blackburn Rovers in the 2013 quarter-finals.</p>
<p>The visitors defended superbly to frustrate Arsene Wenger’s Gunners as Gervinho, Tomas Rosicky, and Theo Walcott all came close to either opening the scoring or equalising late on.</p>
<p>Blackburn’s winning moment came with 20 minutes remaining when Colin Kazim-Richards reacted the sharpest to Martin Olsson’s saved effort.</p>
<p>Kazim-Richards’ scuffed rebound went in off the post to give the visitors the lead and despite Wenger throwing on a few of the big guns in the closing stages, Blackburn defended resolutely to preserve their advantage.</p>
<p><em>Continued on the next slide…</em></p>
<div class="next-slide slider"> <a class="next-slide-btn" style="background: #c01f2f" data-track="shortcode" data-track-action="next-slide-shortcode" href=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"#"> <span class="title">Next:</span> #4 biggest FA Cup upset </a>
</div><!—pageview_candidate—><hr id="pagebreak"><h2>Nottingham Forest 4-2 Arsenal (2018)</h2>
<div class="embed embed-video"><iframe loading="lazy" width="500" height="281" src=https://paininthearsenal.com/2023/01/09/arsenals-5-biggest-fa-cup-upsets/4/"https://www.youtube.com/embed/l6Sp-BcGJzI?feature=oembed%22 frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen title="Emirates FA Cup Third Round: Nottingham Forest 4-2 Arsenal"></iframe></div>
<p>Arsenal enjoyed plenty of FA Cup success throughout the 2010s as they lifted the trophy four times.</p>
<p>However, the Gunners also suffered one or two bleak eliminations and their defeat at the City Ground in 2018 epitomised the depths to which Arsenal had sunk under Wenger. This was prime AFTV.</p><div class="widget fs_ads"> <div class="fs_ad_widget-ad" style="margin:0 auto; width: 300px;"> <div class="fs-ll-ad" data-ad-type="minutemedia_slideshow_inline_300x250__desktop__tablet" data-vendor="minutemedia">
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<p>This was a classic cup tie that the visitors were on the wrong side of. An Eric Lichaj brace handed the second-tier outfit a 2-1 half-time lead before the Gunners conceded a pair of second-half penalties to put the tie beyond them.</p>
<p>The eventual 4-2 defeat was just another miserable episode towards the end of Wenger’s tenure as a wave of toxicity clouded over the club.</p>
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<p>How times have changed, eh?</p><!—pageview_candidate—></p>">
