Arsenal’s Best Underdog Victories – Against All Odds

Every so often Arsenal pull off a win that leaves even the most hardened fans blinking in disbelief. These are the nights when the Gunners, tipped to lose, rewrote the script and sent waves through the football world.

Some of these triumphs still give me goosebumps, it feels like magic every time.

Title Decider at Anfield (26 May 1989)

Picture it: Anfield, the last game of the season, Liverpool only needing a draw to clinch yet another title. Arsenal had to win by two goals. Alan Smith gave the Gunners a 52nd-minute lead, but nerves kept jangling until the final whistle. Then, in the 90th minute, Michael Thomas swept in that second goal. Cue pandemonium. Nobody saw it coming, certainly not the bookmakers who had Arsenal as rank outsiders. And yet, there it was, Arsenal lifting the trophy, statuesque with relief and disbelief.

Old Trafford Shock (8 May 2002)

Manchester United at home, Arsenal needing a win to secure the title, yet the hosts were favourites. Sylvain Wiltord stepped up in the second half, nodded home a delicate winner and sent Old Trafford into stunned silence. It was not just the goal, it was the way Arsenal defended tooth and nail, leaving United scratching their heads. That solitary strike clinched Arsenal’s second Premier League crown under Arsène Wenger and completed an unbeaten away record.

San Siro Slaying (25 November 2003)

Hands down one of the most memorable victories. Arsenal arrived in Milan during the Invincibles era but were still considered massive underdogs. Inter boasted stars galore, dominated possession and peppered the box. Yet Wenger’s men ripped them apart 5-1. Thierry Henry scored twice, with Ljungberg and Pires also on the scoresheet. Even the most surprised football bookmakers must have been up all night revising their odds.

Bernabéu Brilliance (21 February 2006)

Real Madrid, the Galácticos, at the Santiago Bernabéu. In most stories, Arsenal would have folded. Thierry Henry had other ideas. A perfectly weighted solo run in the second half and he found the net past Iker Casillas. One-nil, aggregate win, and Arsenal progressed without a second-leg scare. It was a moment of grace, audacity and stunned silence from thousands of Madridistas.

Arsenal vs Barcelona (16 February 2011)

When Barcelona’s maestros, Messi, Xavi and Iniesta, arrived at the Emirates, Arsenal looked the weaker side. David Villa’s opener seemed to seal the narrative. But late on, Robin van Persie – one of the top 5 Arsenal strikers of all time – flicked home an equaliser before Andrey Arshavin bent in the winner. Two goals in the final 12 minutes turned the tie on its head. It was a brief, dazzling rebellion against the inevitability many had predicted.

From Anfield to the Bernabéu, these victories have their own mythic quality. They remind us why football’s beautiful unpredictability holds such a grip on our hearts. And hey, if you need a palate cleanser after reliving these heart-stoppers, check out some Arsenal funny moments to lighten the mood—because sometimes a good laugh is the best way to celebrate the impossible. 

Which underdog victory tops your list? Drop your thoughts below and let’s relive the magic together. 

Which underdog victory tops your list?

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