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13 of the most disastrous debuts in football history ft. Caicedo, Woodgate & Messi…

You only get one chance to make a first impression in football, but former Chelsea, Manchester United and Real Madrid stars made debuts that were memorable for all the wrong reasons.

In any workplace, your first day is a case of getting your head down, doing your job and trying not to f*ck things up. Alas, that’s often easier said than done considering the pratfalls that this lot fell into.

We’ve trawled through the archives to bring you 13 of the worst debut performances in football history.

Moises Caicedo

Chelsea broke the British transfer record to sign Caicedo for £115million after a comedy bidding war with Liverpool, creating a million memes and allowing their supporters a period of glorious gloating.

Any sense of satisfaction instantly diminished after the Ecuadorian’s debut at West Ham; appearing as a late substitute, Caicedo was miles off the pace, made numerous mistakes and conceded the penalty that confirmed Chelsea’s 3-1 defeat.

The only way is up. Right?

Jonathan Woodgate

No notes.

Jonathan Woodgate during a Real Madrid training session at Valdebebas, Madrid. August 2005.

READ: Remembering Jonathan Woodgate’s calamitous Real Madrid debut

Lionel Messi

Arguably the greatest footballer of all time, Messi was sensational as he led Argentina to glory at the 2022 World Cup – but his international debut was one to forget.

The forward was given his first call-up for a friendly against Hungary by manager Jose Pekerman, coming off the bench in the 63rd minute.

However, rather than impress as a substitute, Messi was instead sent off just two minutes after entering the field after a foul on Hungary’s Vilmos Vanczak.

Messi was reportedly found in tears in the changing room after being sent his marching orders, but we’re betting it doesn’t keep him up at night these days.

Thiago Silva

Thiago Silva is one of Chelsea’s best signings of the modern era, but his bow in English football was extremely inauspicious.

Away at newly-promoted West Brom, the Brazil international lost possession in his own half and allowed Callum Robinson to score the second of the Baggies’ three first-half efforts.

He also failed to make a single tackle and was dribbled past twice. But goals from Mason Mount, Callum Hudson-Odoi and Tammy Abraham in the second-half bailed the veteran defender out and he’s barely looked back since.

Patrice Evra

Evra joined United in January 2006 and went on to enjoy a superb career at Old Trafford, winning 14 trophies – including five Premier League titles and the Champions League – and played 379 times for the Red Devils.

Which all seemed unlikely after being hooked at half-time on his United debut, following 45 minutes of getting the run around by Trevor Sinclair as Sir Alex Ferguson’s side lost to Manchester City.

“After the first five minutes I played against Trevor Sinclair,” Evra said in 2022. “I was cut here [on the head] I remember I was against the post and you know when you’re talking to yourself, I was like ‘what the hell am I doing here?’

“The football was so fast, so strong. I was chilling in Monte Carlo – I was named the best left-back four times. I was thinking I’d made it, that I was a big player. Then at half-time, that’s the first time I was introduced to the hairdryer by Sir Alex Ferguson.

“He destroyed everyone and he came to me and said, ‘You’re going to sit next to me and you’re going to learn English football’. I’ve played for the French national team, I’ve been in the final of the Champions League – and on my first game I’ve been subbed after 45 minutes.”

Joe Cole

Cole’s red card on his Liverpool debut against Arsenal in 2010 was probably the highlight of his spell at Anfield – neither Cole nor the Reds supporters particularly warmed to each other and he remains one of the club’s most underwhelming signings.


When Arsenal signed Gervinho from Lille in 2011, after being linked with his then team-mate Eden Hazard for most of the window, their fans were hopeful that the winger would be almost as good as the Belgium forward.

It was an illusion that lasted just one match after Gervinho was sent-off for slapping Joey Barton in a goalless draw at Newcastle. In fairness, few would begrudge him for landing one on Barton’s chops.

Ali Dia

Rumour has it that Dia’s only appearance for Southampton set Matt Le Tissier on course to become Britain’s biggest crank.

Southampton manager Graeme Souness.

READ: I rewatched Ali Dia’s one game & realised he wasn’t *that* bad

Saul Niguez

Although he’d fallen out of favour under Diego Simeone, Saul was still considered one of Europe’s most talented midfielders when he joined Chelsea on loan from Atletico Madrid in 2021.

But he was completely overrun by John McGinn and the Aston Villa midfield on his debut, while two stray passes almost led to Ollie Watkins finding the back of the net.

Saul was hooked at half-time and started just four more league games during his season-long loan move.

Gaetano Berardi

Berardi became a cult hero at Leeds despite, or perhaps because, he marked his debut with a red card for a jaw-dropping karate kick against Accrington Stanley.

“I didn’t feel anything,” Will Hatfield, recipient of Berardi’s Jackie Chan impression, told The Square Ball in 2023. “He never actually put his two feet together. He sort of wrapped his legs around, so I didn’t really feel much contact.

“I didn’t go down and make a meal of it. I was so surprised. I was just thinking, ‘What’s he actually doing? Why has he done that?’

“Being a Leeds fan, I didn’t want to start causing a stir and pushing to start a fight. Because I was young as well, I thought, ‘Do you know what, I’m just going to keep quiet here.’

“If he did that to me now, ten years on, I’d make a bit of a meal of it and probably square up to him. You know what it’s like in football, handbags. I’d have liked a bit of argy-bargy with him.

“I was only young and I didn’t want to upset the Leeds fans, so I just thought I best not do anything. It was a really strange one. I’ve never had that in my career since. It was funny how it happened.”

Rio Ferdinand

Leeds set a new British transfer record and made Ferdinand the world’s most expensive defender upon his £18million move to Elland Road from West Ham in 2000.

But his club bow was a chastening one. After David O’Leary rejigged his Leeds defence to accommodate their new signing, mid-table Leicester raced into a three-goal lead within 28 minutes.

Conceding goals to Robbie Savage, Ade Akinbiyi, and Gerry Taggart wasn’t in the script. Leeds would miss out on Champions League qualification that season, starting their doom spiral to League One.

Wayne Bridge

Deep in relegation trouble at the start of 2011, West Ham turned to the experience of Wayne Bridge to stabilise their defence and kickstart their march to safety.

Fat chance; the England defender endured a terrible time as he looked well off the pace and was at fault for the first two goals that Arsenal scored.

If that alone wasn’t bad enough, he also gave away a late penalty that helped Arsenal secure a 3-0 win. West Ham were relegated in bottom place.

Alex Jankewitz

We’ve saved the worst until last; Jankewitz lasted 79 seconds of his Premier League debut for Southampton against Manchester United in February 2021 before being red-carded for a dangerous tackle on Scott McTominay.

Southampton lost 9-0. Jankewitz never played another match for the club and was sold to Young Boys that summer.

READ NEXT: The 14 Barca players who made their debut in the same season as Messi

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