Ben Woodburn, Liverpool's youngest-ever goalscorer, has ended his 16-year association with the club. The 22-year-old entered the Anfield record books back in November 2016 when he scored in a League Cup win over Leeds United.

Woodburn's strike came at the tender age of just 17 years and 145 days - a record that still proudly stands. But his contract expired this summer and the midfielder is now starting afresh after winning a deal at Championship side Preston North End.

It appears Woodburn will be missed by one player in particular on Merseyside. The Wales international took to social media to confirm his exit and Reds' defender Trent Alexander-Arnold was quick to send his pal a good luck message.

Alexander-Arnold, a year older than Woodburn, came through the ranks with the midfielder and they are close friends. He responded to Woodburn's message by saying: "My brother what a journey," followed by a heart emoji.

Speaking to Liverpool's website back in 2017, after being integrated into the first team, Woodburn delivered an insight into their close friendship, saying: "It makes it easier when one of your mates is with you in the squad.

I can chill with him all the time. It's not like going into the squad and not knowing anyone… if you're with your mate, it's a lot easier. It is great to see when someone who you know and who you've basically grown up with is doing well as well. It's so nice to see."

At the time both youngsters were catching the eye and although only Alexander-Arnold has gone on to become a key figure in Jurgen Klopp's side, both he and Woodburn earned plaudits from assistant Pep Lijnders for their attitude and application.

The Dutchman said of the pair: "I use Ben and Trent as an example often because they really are one. They help prove a lot of modern misconceptions in football wrong: that you have to be a certain age, a certain size, that you first have to go on loan and so on before you can get into the first team.

If you see them after each session and how long they stay on the pitch - not just shooting on goal, crossing and heading and doing the nice things - they always challenge each other to become technically and tactically better."

Woodburn ultimately failed to stay at the top level after his early career breakthrough, enduring a number of unsuccessful loan spells away from Anfield. After joining up with Ryan Lowe's North End on trial, he impressed sufficiently to be awarded a one-year contract and is now hoping to prove a point at Deepdale.