Wild scenes in the Portuguese second division saw Paris Hilton's brother-in-law, Courtney Reum, make his professional debut for Lank Vilaverdense at 45-years-old.
Reum, is a friend of the club's owner, Canadian Adrian Johansson and was given the chance to take to the pitch in a competitive game for the now-relegated side after becoming an investor.
The American had never played professional sport and was the oldest member of the team when he was named on the bench for their league clash against Torreense on Sunday.
Hilton married his brother, Carter Reum in November 2021, with the couple later welcoming their first child together last year.
Wild scenes in the Portuguese second division saw Paris Hilton 's brother-in-law, Courtney Reum, make his professional debut for Lank Vilaverdense aged 45
Reum (left) is the brother-in-law of Hilton (right) who is the heiress to the global Hilton hotel chain
But his presence on the football pitch angered club supporters who watched their team relegated to Portugal's third division after being relegated following their latest 1-0 defeat.
The bizarre scenario arose as Reum signalled ambitious plans to help the club climb up the Portuguese league pyramid, with his introduction in the 85th minute of Sunday's match evidently an attempt to sweeten his interest in the club.
Reum was surprisingly defiant about his new status as a professional footballer and admitted his age meant he could 'add value' to the team while he also compared himself to Portuguse superstar Cristiano Ronaldo who is still playing at the age of 39.
Leading up to the moment that saw Reum make his debut at the weekend, the American confidently said: 'I try to be in good shape, I was faster when I was younger, but I can be competitive and add value. I'm getting ready to play, I feel stronger every day.
'[Cristiano Ronaldo] is almost my age,' he further claimed in a giddy schoolboy-like manner.
Posting a training video of himself on social media, Reum confirmed he was set to make his first appearance for the club, stating: 'Yes, the rumors are true. I’m entering my Ryan Reynolds Welcome to Wrexham x Ted Lasso era with a twist and making my professional football debut (as possibly the oldest person ever to do so at this level) in Portugal for Lank FC Vilaverdense on May 4th.'
Former Vilaverdense player, Carlos Lomba, hit back, replying: 'Me being a former player of this club Lank Vilaverdense, I’m extremely sad to see how ridiculous football is becoming!
'This is a huge disrespect to all the footballers that actually have quality and fight daily for an opportunity!
'This is not your fault, but from the ones that allowed you to do this nonsense,' he said.
Reum previously announced he was making his debut for the Portuguese club on May 4th
Former Vilaverdense player Carlos Lomba described the decision to recruit Reum as 'nonsense'
The 45-year-old American made his debut in the 85th minute of the team's 1-0 defeat
Back Stateside, Reum is a businessman, investor and author where he has wrote books on how to achieve success, but his main focus has been football ever-since he joined the club in January.
Lank Vilaverdense previously stated at the start of the year that Reum had joined the club on the advice of the club's scouting department, but the striker looked at odds with what was going on when he came on against Torreense.
Reum - wearing the No.78 shirt - was brought on as a double-substitution and was seen being given instructions by his team-mates as he failed to make much of an impact on proceedings.
Reum told Wrexham owner Ryan Reynolds to try and do the same as him by getting on the pitch for the team
Reum even compared himself to legendary Portuguese player Cristiano Ronaldo
The experience of playing in a competitive league game for the club situated just outside Braga has angered some in football, but Reum advised other investors to do the same as he instructed Wrexham's Ryan Reynolds to try and get minutes for the newly-promoted Welsh team that he co-owns with Rob McElhenney.
'But Ryan Reynolds isn't playing. I think he should try playing for Wrexham or maybe we could have a game at the end of the season between the two teams,' he said.
Vilaverdense manager Sergio Machado admitted the decision to bring Reum on was 'tough' but insisted he did so to protect other players in the group.
'In the last minutes I made a decision not as a coach, but as the father of this group. It was tough, but I had to look out for the good of my children. These last 10 minutes help a lot so that my players don't go through what they went through again.'