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Home / Automobiles / Anfield 89, League Cup thrillers: The best Arsenal v Liverpool matches ever

Anfield 89, League Cup thrillers: The best Arsenal v Liverpool matches ever

Arsenal vs Liverpool is a meeting between two of English football’s most decorated teams.

These two sides have played out some classics over the years, and we have taken a look back at some of the greatest clashes between the clubs.

For this list, we’ve picked out the top 8 matches, ordered solely by the amount of pure drama that has unfolded across meetings in the league, cup, and in Europe. There has certainly not been any shortage of that over the years…

8 Arsenal 3-2 Liverpool, October 2022 Gunners continue title tilt with dramatic victory

Martinelli 1′

Nunez 34′

Saka 45+5′

Firmino 53′

Saka pen 76′

The 2022/23 campaign saw both these clubs reverse their fortunes somewhat, as perennial title challengers Liverpool were eventually left to settle for a Europa League place, while the Gunners almost took champions Manchester City all the way in the race for the Premier League.

Back in the autumn of 2022, the Gunners were on a roll under Mikel Arteta, winning seven of their first eight games, with over twice as many points as their opponents heading into this one.

And the events on the pitch looked to have followed the form book when Gabriel Martinelli opened the scoring inside a minute, only for Darwin Nunez to strike back for the visitors.

Bukayo Saka edged the Gunners in front on the stroke of half-time before Roberto Firmino netted a second equaliser.

There was a little controversy surrounding the winner, with Thiago adjudged to have fouled Gabriel Jesus in the box, leaving Saka with the opportunity to hand the home side the lead once more from the spot – one that he did not pass up as he settled an enthralling encounter.

The Gunners held on in a rare Premier League success for the north Londoners – it remains their only league win over Liverpool since the summer of 2020.

7 Liverpool 3-6 Arsenal, January 2007 Arsenal’s young guns school shellshocked Reds at Anfield

Fowler 33′

Aliadiere 27′

Gerrard 68′

Baptista 40′

Hyypia 80′

Song 45′

Baptista 45′

Baptista 60′

Baptista 84′

Neither of these clubs had much to write home about by the end of this campaign, with Liverpool and Arsenal both losing finalists in the Champions League and League Cup respectively while both sealing their places in the top four.

But en route to the Carling Cup final in Cardiff that year, the Gunners came up against a Liverpool side they had beaten just three days earlier in the FA Cup, hoping history would repeat itself. It would – and then some.

A Tomas Rosicky double and a Thierry Henry special helped Arsene Wenger’s side over the line on the preceding weekend, but as was customary in the League Cup in those days, the Frenchman let those on the fringes of the first team take centre stage for this quarter-final.

No one did that more so than on-loan Sevilla forward Julio Baptista, who netted four that night at Anfield to seal a semi-final against Tottenham Hotspur.

Baptista was greatly aided by Jeremie Aliadiere, who opened the scoring, while Alex Song’s goal helped to secure a commanding 4-1 half-time lead as the Gunners cancelled out Robbie Fowler’s equaliser.

The Brazilian helped himself to a second-half double – while missing a penalty – to complete the flood of goalscoring, with Steven Gerrard’s emphatic volley and Sami Hyypia’s header mere consolations on a bizarre night on Merseyside.

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ByJack Salveson Holmes 6 Liverpool 5-5 Arsenal, October 2019 Reds prevail as ten-goal bonanza settled by spot-kicks

Mustafi og 6′

Torreira 19′

Milner pen 43′

Martinelli 26′

Oxlade-Chamberlain 58′

Martinelli 36′

Origi 62′

Maitland-Niles 54′

Origi 90+4′

Willock 70′

There must something in the air when these two meet in the League Cup, though Jurgen Klopp’s side were not to make the same mistake when Arsenal’s youngsters threatened to play them off the Anfield park again.

Liverpool had not long been crowned European champions, while Arsenal were in their second season under Unai Emery, who had already tasted heavy defeats from Klopp’s men by this point.

And it looked like it would be the same again when Shkodran Mustafi put through his own net to give the hosts the lead, but within half an hour, the Gunners were 3-1 up thanks to Lucas Torreira and a brace from Gabriel Martinelli, who was making a name for himself in the cup competitions.

James Milner’s penalty reduced the arrears as the teams continued to trade goals galore, with Joe Willock’s strike – Arsenal’s fifth – the pick of the bunch.

There was an air of inevitability about the Liverpool equaliser, but it nevertheless came four minutes into added time from Divock Origi, who notched his second of the night to take the game to penalties.

Dani Ceballos was the man to fluff his lines from the spot as Liverpool edged what was another cup classic.

5 Arsenal 1-1 Liverpool, April 2011 Liverpool ruin Arsenal title challenge after two extraordinary twists

Van Persie pen 90+8′

Kuyt pen 90+12′

Arsenal still had hopes of title glory heading into this one – the Gunners were hoping to cut Manchester United’s lead at the top to just four points ahead of a title tussle at the start of May, while Liverpool were in transition having dismissed Roy Hodgson earlier in the campaign, with Sir Kenny Dalglish back in the dugout.

The Gunners will have thought they had snatched it late on when Robin van Persie struck home a penalty deep into stoppage time – owing to a serious injury to Jamie Carragher – to send the Emirates crowd berserk.

However, the party atmosphere was swiftly dampened when a clumsy Emmanuel Eboue was deemed to have fouled Lucas Leiva in the area following a Liverpool free kick which ought to have been the final kick of the game.

Alas, referee Andre Marriner would point to the spot, allowing Dirk Kuyt to smash home the latest of late equalisers – his 102nd-minute goal was the latest ever recorded in the Premier League.

Arsenal would later collapse to fourth place, while Liverpool recovered somewhat the following year by making two cup finals under Dalglish.

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ByMark Marston 4 Arsenal 1-2 Liverpool, May 2001 Owen double breaks Arsenal hearts as Houllier’s cup kings triumph

Ljungberg 72′

Owen 82′

Owen 87′

2001 was a special year for Liverpool; while they may not have had the league success craved by many, they did manage to secure the next best thing: a cup treble.

The first part of that treble was secured in February 2001, when Gerard Houllier’s side saw off First Division outfit Birmingham City on penalties at the Millennium Stadium. Returning to the same venue to make it two from two, they didn’t look like doing that when Freddie Ljungberg put Arsenal ahead with less than 20 minutes remaining.

But Michael Owen managed to single-handedly turn the game on its head, with the striker stabbing the ball home to equalise late on before an even later winner securing what had looked an unlikely comeback. It left Arsenal empty-handed for the season, though they would bounce back by lifting the Premier League the following year, with Liverpool in second.

The Reds would go through even more drama on their way to the UEFA Cup, beating Alaves 5-4 in Dortmund after extra-time.

3 Liverpool 4-2 Arsenal, April 2008 Gerrard and co edge Gunners in Champions League classic

Hyypia 30′

Diaby 13′

Torres 69′

Adebayor 84′

Gerrard pen 86′

Babel 90′

Liverpool may have been slight favourites for this Champions League quarter-final second leg, with the Reds taking an away goal into the deciding tie at Anfield, which started level at 1-1.

This game was part of a so-called trilogy, with Arsenal and Liverpool going head-to-head at the Emirates twice in a week in Europe and the Premier League before the winner-takes-all clash three days later. While both prior games ended 1-1, there had to be a winner one way or another here.

The first leg had its fair share of chaos, with Alexander Hleb denied what looked a stonewall penalty and Nicklas Bendtner inexplicably blocking the ball from going into Liverpool’s net. The second was just as frantic.

Arsenal set their stall out early by nicking an away goal for themselves thanks to Abou Diaby, only for Sami Hyypia to level things up on the night and on aggregate.

Fernando Torres then gave Liverpool their first true lead in the tie when he smashed home, until a magical, mazy run from Theo Walcott cut through almost the entire Liverpool team as he squared for Emmanuel Adebayor to net a second away goal for Arsenal, who were less than ten minutes away from a semi-final date with Chelsea.

But the kings of Europe found a way, albeit through a contentious-looking penalty decision as Ryan Babel was felled by Kolo Toure. Gerrard was on hand to send Anfield into raptures, and with Arsenal desperate for another equaliser, they were hit on the break again as Babel ran clear to settle the tie once and for all.

2 Liverpool 4-4 Arsenal, April 2009 Four-goal Arshavin dents title hopes for title chasers Liverpool

Torres 49′

Arshavin 36′

Benayoun 56′

Arshavin 67′

Torres 72′

Arshavin 70′

Benayoun 90+3

Arshavin 90′

While scoring four at Anfield was nothing new as far as Arsenal strikers were concerned, it’s difficult to look past Andrey Arshavin’s quadruple and the ding-dong game that ensued as the Reds looked to hunt down Manchester United in the Premier League title race.

Despite losing just twice all season, Liverpool were only a point behind the Red Devils and had already played a game more than the then-champions, so three more were much-needed here.

Unfortunately, Arsenal were having a decent campaign on the road, having beaten Chelsea away from home and seen off the likes of Roma on the way to the Champions League semi-finals.

So despite having little to play for in the league and big ties on the horizon, Arsenal certainly didn’t show it, with Arshavin handing the Gunners a precious half-time lead.

Yossi Benayoun and Torres hauled Liverpool in front before the Russian struck twice more – the first of those being an absolute screamer past Pepe Reina.

Torres netted an equaliser to set up a grand finale, during which Walcott raced away in similar fashion to his exploits in the previous season and laid it on a plate for Arshavin’s fourth in the 90th minute.

However, Arsenal would again surrender their advantage as Benayoun popped up at the death to momentarily take Liverpool top of the league, but it was not enough come the end of the campaign, with both clubs ending promising seasons trophyless.

1 Liverpool 0-2 Arsenal, May 1989 “It’s up for grabs now…”

Smith 53′

Thomas 90′

There could really only be one game to round off this list. Considered by some to be the greatest league finale of all time – even in light of Sergio Aguero’s title-clincher in 2012 – the heroics of this Arsenal team have been etched into every Gunners fan’s psyche and even immortalised on film.

Despite boasting a sizeable lead at one stage, Arsenal were letting their league challenge slip, so much so, that Liverpool – champions in 9 of the previous 13 seasons – had almost everything in their hands heading into the final match of the campaign, as only a two-goal defeat would see the Gunners nick the title from under their noses.

It was indeed an emotionally charged night at Anfield, with the game being held back due to the tragic events at Hillsborough just six weeks before; Arsenal players entered the field with flowers to mark their respects.

Going in goalless at the break, it was all going to plan for the hosts, although Alan Smith’s contested header early in the second half left the tie, and indeed the championship, on a knife-edge.

For Arsenal, it was a case of striking at the perfect moment. Having held out the likes of Ian Rush, John Barnes and John Aldridge at the other end, they went in search of the elusive second goal well into stoppage time.

Midfielder Mickey Thomas – who would later don the colours of Liverpool – proved to be the Anfield side’s nemesis, as he picked up Alan Smith’s lofted pass and slotted past Bruce Grobbelaar to snatch the First Division from Liverpool’s grasp in the most dramatic fashion possible.

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