Liverpool face the tricky task of overcoming Porto in the last 16 of the Champions League, starting with Wednesday night’s first leg in Portugal.

The side haven’t been past this stage since the 08-09 season when they reached the quarter-finals of the competition before losing 7-5 on aggregate to Chelsea over two epic legs.

But the Merseyside club topped Group E with an unbeaten record and are the second top scorers in the Champions League this campaign, behind PSG.

Liverpool’s opponents came second in Group F, behind surprise package Besiktas, and are unbeaten in 21 Portuguese Primeira Liga games so far this season.

They also boast a good home record against English opposition having only lost three of 16 – although those three defeats did come in their last four clashes.

What time does it start?

Porto vs Liverpool kicks off at 7.45pm on Wednesday night at the Estádio do Dragão.

Where can I watch it?

The match will be shown live on BT Sport 2 from 7pm. Highlights will be shown at 10.45pm on ITV 1, Wednesday night.

It’s a big game for…

Virgil Van Dijk. The £75m centre back was meant to be the final piece of the puzzle for Liverpool in their pursuit of defensive solidarity but it hasn’t quite proved that way just yet.

But, the Dutchman performed amicably at the weekend, despite the torrent of abuse thrown his way upon his return to St Mary’s as Liverpool cruised to a 2-0 victory at Southampton.

Now it’s time for Van Dijk to prove himself on the European stage again as Liverpool face their biggest challenge yet in the Champions League.

Time for the defender to prove himself on the European stage (Getty Images)

Weird stat…

5. The Champions League may be filled with an array of world-class, jaw dropping talent and yet, topping the assist charts so far this campaign with five is Liverpool’s stand-in left-back, James Milner.

Remember when…

Liverpool defeated Porto 4-1 in the clubs’ most memorable clash at Anfield in November 2007 to keep the Red’s hope of passage to the knockout stage alive.

A brace from Fernando Torres, a Steven Gerrard penalty and a late Peter Crouch header sealed the three points.

Player to watch…

Vincent Aboubakar. The Cameroon international has been in scintillating form for Porto this season, netting 26 times in 32 games in all competitions.

In the Champions League alone Aboubakar scored five goals in five games and assisted twice, including a pair of braces home and away against Monaco.

Liverpool have a frightening attack of their own with Salah and Firmino scoring freely but they must be cautious of opening up too much because Aboubakar will not relent in front of goal.

Vincent Aboubakar has been in scintillating form for Porto (Getty)

Past three meetings…

Liverpool 4 Porto 1, Champions League, November 2007

Porto 1 Liverpool 1, Champions League, September 2007

Liverpool 2 Porto 0, Uefa Cup, March 2001

Form guide…

Porto: WWWDDW

Liverpool: WDWLLW

Odds…

Porto to win: 41/20

Liverpool to win: 13/10