From Selhurst Park ballboy to Anfield debutant Liverpool’s forgotten summer signing Freddie Woodman ready for his moment.
For Freddie Woodman, Wednesday night might be more than just a first competitive appearance for Liverpool it could be the culmination of a footballing journey that began as a wide-eyed south London kid watching from the stands at Selhurst Park.
The 28-year-old goalkeeper, who joined Liverpool quietly on a free transfer from Preston North End in the summer, is in line to make his debut when Arne Slot’s side face Crystal Palace in the Carabao Cup fourth round at Anfield.
With Alisson Becker sidelined by a hamstring injury and Giorgi Mamardashvili expected to be rested, the fixture has presented Woodman with the kind of opportunity that seemed a world away just a few months ago.
And for a player who once served as a Palace ballboy and mascot, the opponent only adds to the significance.
Woodman’s move to Merseyside was one of the quieter stories of Liverpool’s summer. Amid headline arrivals and departures, his signature represented the kind of subtle, strategic squad-building that sporting director Richard Hughes has come to value.
“I wanted to keep playing and I’m only 28,” Woodman told Liverpoolfc.com. “But there was a conversation in the summer where Liverpool came up. I had other options but my dad said to me, ‘How do you turn down Liverpool? You just can’t do it.’ I’m very happy with my decision.”
That advice came from someone who knows the business well. His father, Andy Woodman, played professionally as a goalkeeper and is now the manager of League Two side Bromley. The pair remain close, often dissecting performances and training routines together.
“My dad has been a massive influence,” Freddie said. “He’s lived it, so when he gives advice it’s never sugar-coated he tells you straight. When Liverpool showed interest, he just said it’s one of those clubs you can’t say no to. He was right.”
When Liverpool completed the signing in early July, there was no grand unveiling or glossy social media announcement just a quiet announcement confirming the arrival of a player with more than 200 EFL appearances and four Premier League outings for Newcastle United.
His addition made sense for multiple reasons. The departure of Vitezslav Jaros on loan to Ajax left a gap in the goalkeeping department, while Alisson’s workload required experienced cover beyond Mamardashvili.
For Woodman, the move was both pragmatic and emotional a chance to be part of something bigger.
“I’ve spent a lot of time playing in the Championship so to play for a club with this history is pretty special,” he said. “Any time I get to pull on the jersey for this club, whether it be a pre-season game or whatever competition, I’ll always just try to do my best and enjoy the moment.”
It’s the kind of humility that fits Liverpool’s modern goalkeeping culture one built on quiet professionalism and internal competition rather than noise.
Liverpool’s domestic cup campaigns have often been shaped by their goalkeepers. From Pepe Reina’s shootout heroics in Cardiff to Caoimhín Kelleher’s emergence as a cult hero at Wembley, the club’s goalkeeping lineage is rich with moments of redemption and recognition.
Woodman knows it too well.
“It’s clear that this club takes the competition seriously, like it does every competition,” he said. “When you get to the latter stages, you go to Wembley and you see how important it is to the fans.”
Liverpool’s relationship with the Carabao Cup has been particularly strong in recent years. The Reds have lifted the trophy a record 10 times, most recently in 2024 when they beat Chelsea 1-0 at Wembley. They were beaten finalists last season, losing 2-1 to Newcastle United in the final.
And for goalkeepers at Anfield, the competition carries unique symbolism.
“We train in the goalkeeping area at the AXA Training Centre and I regularly see the photo of Caoimhin Kelleher on the wall after his success in the recent finals,” Woodman added. “That’s how important it is. You can really write yourself into history if you win trophies at this club.”
It’s easy to forget that Woodman was once one of England’s most promising young goalkeepers. A former England Under-21 international, he won the Under-20 World Cup with the Three Lions in 2017, saving a penalty in the final against Venezuela.
But his club career took a different path — a patchwork of loans, resilience and reinvention. Spells at Crawley, Kilmarnock, Swansea and Preston forged a player comfortable with the grind of the EFL and the unpredictability of football outside the elite.
At Preston, he was a fixture 138 appearances in all competitions, often the standout in a team punching above its weight. His performances caught the attention of several Premier League sides, but it was Liverpool’s proposal, delivered personally by Hughes while Woodman was on holiday, that felt right.
The timing, as much as the badge, was key.
Wednesday night’s fixture offers a narrative that even Woodman admits feels almost scripted. Born in Croydon, raised on Palace’s doorstep, he spent his formative years at the club’s academy.
“After a school session, a coach came up to me and said he wanted me to go down to Crystal Palace Park, where the academy set-up was based, that evening and take a trial. And that’s where it all started for me,” he recalled.
“I used to go down to Selhurst with my grandad as he had a season ticket down there. I was a ballboy a few times and also a mascot and I just used to love it. Being a south London lad, being a Crystal Palace fan was just born into me really.”
Facing the team that shaped his football upbringing, in a Liverpool shirt at Anfield, will feel surreal but also richly earned.
Arne Slot has shown faith in rotation during cup competitions. Last season, Kelleher started six matches en route to the final, a tradition inherited from Jürgen Klopp’s tenure and one Slot appears set to continue.
For Slot, it’s also a chance to give his team much-needed confidence. Liverpool have lost four consecutive Premier League games, and the Carabao Cup now offers a different kind of stage: one where a win could reset the rhythm of a faltering campaign.
For Woodman, the stakes are simpler but no less meaningful. He hasn’t played a competitive fixture since March If he performs well, there’s every chance he earns further minutes in the FA Cup.
But on Wednesday, he’ll stand under the lights at Anfield the same stadium where generations of Liverpool goalkeepers have made their names knowing that his chance, however brief, has finally arrived.
“You can really write yourself into history if you win trophies at this club,” he said. “That’s what it’s about. Moments like that stay with you forever.”
Whether he becomes the next in Liverpool’s lineage of unlikely cup heroes remains to be seen. But for Freddie Woodman, the journey from Selhurst Park ballboy to Anfield debutant already feels like a story worth telling.
