Trent Alexander-Arnold made his first Liverpool start on 25 October 2016 alongside another academy prospect whose career has panned out a little differently.
The right-back was given his chance by Jurgen Klopp in a League Cup tie against Spurs, with Liverpool winning 2-1.
Daniel Sturridge scored twice with Vincent Janssen scoring a consolation penalty.
Alexander-Arnold, who is closing in on 300 appearances for Liverpool, played 68 minutes before he was replaced by Nathaniel Clyne.
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But the night was a memorable one for another youngster as Ovie Ejaria played the full 90 minutes.
He had come off the bench in the previous round away from home against Derby but this was a start under the lights at Anfield.
The midfielder, who spent time in Arsenal's academy, made a total of eight appearances that season.
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His last outing for Liverpool was in the FA Cup against Wolves, where he played 74 minutes in a 2-1 defeat.
He went on loan to Sunderland and suffered relegation to League One before turning out 28 times on loan at Rangers, playing under Liverpool legend Steven Gerrard.
That stint ended prematurely in December 2018 and the England youth international went on loan to Reading for the season in January 2019.
The stay lasted until the end of July because of the extended season due to COVID-19 and ended up becoming permanent for a fee of £3.5 million in August 2020.
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Ejaria signed a four-year deal and was said to be earning £650,000-a-year with the Royals, who he made 72 appearances for following the loan.
A long-term injury problem put him out of action for a whole calendar year but then upon his return, his attitude was criticised by Ruben Selles.
"I am waiting for him to get his form and be able to play games and then I will decide," Selles said in a press conference, as per the Reading Chronicle.
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"He needs to show his best. Right now, he is not injured he is building up form to be able to play. He needs to show that he wants to play for us and is fully ready. He needs to show that he wants to play and do things for this football club."
Ejaria built up his fitness training with the Under 21's but he was then quietly released by the club last month.
His contract was due to expire in the summer, with Reading citing his release due to "injury and fitness problems limiting first-team action, and a desire from the club to reduce its expenditure."
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Evaria's last appearance came in November 2022 and he will now be on the look-out for another club.
Featured Image Credit: GettyTopics: Liverpool, Trent Alexander-Arnold, Jurgen Klopp