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Watch: Liverpool’s Last Time Playing in the Champions League Round of Sixteen

As you wait for kickoff against Porto, relive the last time Liverpool made it this far in the Champions League.

Real Madrid v Liverpool - UEFA Champions League Photo by Jasper Juinen/Getty Images

It’s been nine years since Liverpool were in the knockout rounds of the Champions League. Nine long years on the fringes of European football. And the last time out, nine years back less eleven days, the Reds were getting ready to kick off not too far from Porto, just 500km to the west on the Iberian Peninsula.

Liverpool were matched up against Real Madrid for the Round of 16 back in 2009, and despite that they were pushing Manchester United hard in the league and had impressed in the knockout rounds, there was only one favourite heading into that match—and it wasn’t Rafa Benitez’ men in red.

Despite that, they came out as they always did in big matches. Well drilled, organised, in control. Despite Madrid having the run of play, Liverpool limited their chances and kept them mostly to the outside of Pepe Reina’s penalty area. Then, late on, they struck, getting an invaluable away goal.

In the return leg, Madrid knew they needed to play—that they had a deficit to overcome. And Liverpool had the Anfield crowd at their back. The result was a more open game and one that made headlines around Europe as hosts Liverpool dominated their opponents. By the final whistle, it wasn’t even close.

1-0 to the Reds in the first game. 4-0 in the second. 5-0 on aggregate thanks to two of the best performances—albeit two very different performances—Liverpool have had this century. Another strong—if different—outing tonight wouldn’t go amiss. It’s been nine years. Welcome back to the knockout rounds.