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Trent Alexander-Arnold was denied an opportunity to face off against his old teammate Harvey Elliott when the defender's Real Madrid took on Valencia on Saturday.
The right-back has struggled to assert himself in the team under Jose Mourinho this season, with the likes of Denzel Dumfries and Federico Valverde currently preferred in his position.
There have been similar struggles for Elliott, with the Liverpool loanee failing to break into the Valencia team on a regular basis ever since he made the late switch there for the campaign at the end of the summer transfer window.
Recent setbacks have seen both players fail to assert themselves, but with a meeting set up between the former teammates, there was an opportunity to feature in some capacity against one another, whether that was in the starting lineup or from the bench.
Instead, they were denied that opportunity, as Real Madrid opted for Valverde at right-back before subbing on Dumfries, while Valencia decided against bringing Elliott in from the cold after serving his suspension from a red card he picked up late last month.
Los Blancos ended up running out as 3-0 winners on the night, as goals from Valverde, Arda Guler, and Kylian Mbappe sealed another important three points for the visitors on the night. Meanwhile, Los Che had to play the final ten minutes with ten men, after Jose Gaya was sent off.
For Alexander-Arnold, it was a game where, yet again, he had to see two options play ahead of him at right-back, and the fact that one of them scored a key goal only makes it tougher for him to get involved from the start.
There are similar concerns for Elliott, who couldn't be given minutes, even when the game needed a spark from a player like him when he is at his best.
That sets up two similar sets of concerns for both players, who are at a crossroads in their careers, despite hopes of moving on and progressing beyond their time at Liverpool.
Alexander-Arnold's inability to secure a regular place in the Real Madrid team has brought about links with a possible exit, in the hopes of landing more game time. The Reds have been linked with a switch, alongside a whole host of other teams, as the 28-year-old has failed to hit the heights he set at Anfield.
Elliott's circumstances have been slightly more unfortunate, as his failed loan move at Aston Villa has clearly impacted his ability to get on the pitch and show the quality that he has.
There was hope that the Valencia move would give him that opportunity, but so far it has just been filled with more challenges standing in the way of him being a regular starter.
It remains to be seen what follows for the pair, but their denied reunion is another sign of the difficulties that they have faced in their career over the past two seasons.