Chelsea is due to be one of the last clubs to play against a Liverpool team that features Trent Alexander-Arnold when they host the champions-elect at Stamford Bridge in early May.
Albeit, there is some doubt about whether the right-back will be fit to play.
That is because of an ankle injury sustained during their Champions League round of 16 second leg against Paris Saint-Germain.
Arne Slot, however, has said they expect the player back for "the end of the season".
Therefore, if Alexander-Arnold is available, he may play against the Blues twice in two months. That is assuming a free transfer to Real Madrid does materialise.
They are reportedly in talks with the player's representatives over a pre-contract agreement to acquire the right-back when his current deal with Liverpool expires.
That date is June 30, but the problem for Madrid is it falls during the Club World Cup this summer.
So if they are to have Alexander-Arnold play for them in that tournament - as the Daily Mail claims the club are keen to - an agreement for Liverpool to release the player early will have to be made.
If they manage to do so, then he could end up playing against familiar opponents in Chelsea should both teams reach the tournament's latter stages.
The Blues are in Group D, with Madrid drawn in Group H, meaning they cannot meet until at least the semi-finals.
That, though, would require them to win their groups or each end up as runner-ups.
If one comes first and the other second, they will be on opposite sides of the bracket and not meet until the final.
Manchester City will also be in the same scenario if they both win their groups.
But either of them failing to do so with the other finishing first would set up a rematch of their Champions League knockout phase play-off tie at the round of 16 stage.