Jordan Henderson could be set for an emotional first return to Liverpool in the Champions League round of 16. The 34-year-old, who spent 12 successful years at Anfield, is closing in on a stunning January move to AS Monaco.

Henderson left the Reds in summer 2023 to join Saudi Pro League side Al-Ettifaq for £12million and reunite with former teammate Steven Gerrard. However, the England international struggled to adapt to life in the Middle East and had his contract terminated in the January transfer window after making just 19 appearances.

He returned to Europe with Ajax and established himself as a fans' favourite in Amsterdam, playing 12 times at the back end of last season. Henderson has started 24 matches for Ajax so far this term but his time in the Eredivisie is set to come to an end with Monaco on the verge of signing the experienced midfielder.

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According to Fabrizio Romano, a permanent move for Henderson to sign for Monaco is 'almost agreed'. He is set to sign a contract until summer 2026 and become their second transfer of the winter window.

Henderson's proposed move to Monaco is set to see him make a return to the Champions League - the first time he would have played in the competition since his time at Liverpool. And Henderson could now face a return to Anfield in March in Europe's elite club competition.

Monaco finished 17th in the Champions League new format and are set to face a two-legged play-off tie to get through to the last 16. They won four of their eight league matches, drawing the other one.

As for Liverpool, they finished top of the league phase and go straight through to the round of 16, avoiding another two matches that would have added to the schedule.

Arne Slot's Reds will face one of the sides that finished 15th, 16th, 17th and 18th next up, with the quartet first set to be drawn against each other in the knockout phase play-offs.

Prior to the last round of fixtures, Bayern Munich, Real Madrid, Juventus and Celtic occupied such berths - presenting the possibility of a nightmare draw. But fortunately for the Reds, results on Wednesday inevitably ensured such standings switched around.

Paris Saint-Germain and Benfica finished the league phase in 15th and 16th respectively to be seeded for the knockout phase play-off draw. They will each be drawn against either the unseeded Monaco or Brest after they secured 17th and 18th place finishes.

The draw for the knockout phase play-offs will be held on Friday, January 31, but Liverpool won’t find out which of the two winners they will face and which side of the draw they will be on until after the round of 16 draw on Friday, February 21.

If Monaco win their last 16 tie against either PSG or Benfica, there is a real chance that they could draw Liverpool, setting up a dream reunion with Henderson and a return to Merseyside.