Liverpool began 2017 with a frustrating 2-2 draw away at Sunderland on Monday, meaning that they are five points behind Premier League leaders Chelsea having played a game more.

Jurgen Klopp’s men took the lead through Daniel Sturridge and, although Jermain Defoe equalised from the spot, Sadio Mane restored their advantage.

However, Mane then became the villain as his handball allowed Defoe to net another penalty and secure a point for David Moyes’ side, in turn putting a serious dent into Liverpool’s title aspirations.

The result keeps the Reds second in the table, but they are five points behind Antonio Conte’s Chelsea ahead of the Blues’ clash with Tottenham on Wednesday.

By the time Liverpool next play in the league, they could be 11 points behind Conte’s side, and Klopp may need to dip into the January transfer market in a bid to keep their title challenge going in the second half of the season.

If he does, it wouldn’t be the first time that Liverpool have done business in the winter window and, although they have secured some excellent deals, there have also been bad ones.

Thus, here are Liverpool’s WORST THREE January signings since the window came into effect 14 years ago.

Jan Kromkamp

Remember Jan Kromkamp?

The former Dutch international moved to Anfield in an exchange deal with Josemi in January 2006, but never nailed down a first team spot.

Kromkamp made 17 appearances in the second half of the 2005/06 season, but several of these were from the bench, as his defensive vulnerabilities meant that he wasn’t a better full-back than Steve Finnan.

Just eight months after joining the Reds, the defender was sold to PSV Eindhoven, and has since retired from the game due to several serious knee injuries.

Fernando Morientes

There were swathes of optimism around Anfield when the club confirmed the signing of Real Madrid forward Fernando Morientes in January 2005, but it didn’t quite go according to plan for the Spaniard.

Michael Owen had earlier that season signed for the Spanish giants, so bringing in a player of Morientes’ calibre to try and replace the England man was a good move, but it never worked out for the forward.

He managed just 12 goals in 60 games for the Reds, only eight of which were in the Premier League, and was sold to Valencia just 18 months after signing at Anfield.

Morientes spent three years at the Mestalla before signing for Marseille in 2009, and has also had a spell in management with Spanish side Fuenlabrada, although was sacked in February 2016.

Andy Carroll

The Reds had just signed forward Luis Suarez from Ajax in one of their better January transfers, and they then went and spent £35 million on Newcastle forward Andy Carroll as a replacement for the Chelsea-bound Fernando Torries.

However, it was £35 million wasted, as the Englishman managed just 11 goals in 58 appearances for the club, of which only six were in the Premier League.

Carroll netted the winner in their FA Cup semi-final victory over Everton back in 2012, but that was as good as it got for the striker, who moved to West Ham on a season-long loan in that summer.

He has since signed permanently for the Hammers but injuries have once again thwarted his progress, although he has returned to the side in recent weeks.