6 huge deadline day transfers which aged like milk: Antony, Torres, Owen…

Despite having all window long to complete their business, it’s inevitable that clubs end up scrapping around on transfer deadline day and spending big bucks on their top targets.

The ‘magic’ around deadline day – if there ever was such a thing – has faded as years have gone by with reporters being hidden away from fans, Sky Sports News declining at a rapid rate and Saudi Arabia hoovering up players for fun, but no matter what happens, nothing will ever stop seismic deals from going through at the last minute.

A big, last-gasp transfer provides a surreal adrenaline rush for fans in the moment, but they don’t always work out. We’ve compiled a list of X high-profile deadline day transfers which inevitably aged like milk in the sun.

Antony – Ajax to Man Utd

We simply couldn’t start anywhere else. Time is usually the greatest healer of all, but the further we get away from Antony’s £85million move to Manchester United in 2022, the worse it looks.

He actually got off to the perfect start with a goal on debut at Old Trafford as United beat Arsenal, but the wheels very quickly came flying off for the Brazilian who’s book of skills must’ve got lost in the move to Manchester.

Antony has largely flattered to deceive, received criticism from fans for his attitude on the pitch and his lacking ability and, despite Erik ten Hag giving him plenty of games to figure it out, has now lost his place in the side to younger and more talented colleagues.

With just 11 goals and five assists from 83 United appearances at the time of writing, if they were to find a buyer for the winger, they’d be lucky to recoup £20million.

Fernando Torres – Liverpool to Chelsea

One of the original deadline day bombshells, Torres swapped Liverpool for Chelsea for a then-British record fee of £50million in January 2011, making a controversial switch halfway through the 2010-11 campaign.

Despite it being an expensive deal, nobody could fault Chelsea for coughing up for a genuinely world-class forward with a proven firing rate. However, that world-class ability quickly evaded Torres when the Chelsea striker curse kicked in.

He managed just one goal for the rest of the season and wound up on a 24-game goal drought in his first full season at Stamford Bridge. There were high moments such as his finish in the Champions League semi-final against Barcelona, but the lows were simply too drastic and his career never truly recovered from such a poor spell, with him leaving the club in 2014.

Andy Carroll – Newcastle to Liverpool

With Torres heading to Chelsea on deadline day, Liverpool needed a replacement and fast. They threw £35million at Newcastle to sign Andy Carroll before the window slammed shut, a record for a British player at the time.

Carroll immediately took the number nine shirt vacated by Torres, but almost immediately flattered to deceive. He had to wait until April to score his first goals – a brace against Manchester City – and it became quickly apparent in the season that followed that he simply wasn’t good enough to lead the line for the Reds.

He left for West Ham ahead of the 2012-13 season, but not without bagging a late winner against Everton at Wembley to send Liverpool to the 2012 FA Cup final – which they ended up losing to Chelsea. His Liverpool career ended with him having scored just 11 goals in 58 appearances.

Danny Drinkwater – Leicester to Chelsea

A key cog as Leicester City completed a genuine fairytale and won the 2015-16 Premier League, Drinkwater spent another season with the Foxes before getting his big move in the summer of 2017, joining Chelsea for £35million.

He had to wait until October to make his debut due to a thigh injury; the first stutter in a season disrupted by injuries. Drinkwater made just 22 appearances in all competitions and, by his second season, was surplus to requirements under Maurizio Sarri and didn’t make a single Premier League appearance.

Drinkwater only actually left the club permanently in 2022 after loans to Burnley, Aston Villa, Kasimpasa and Reading, retiring a year after his release.

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Matheus Nunes – Wolves to Manchester City

After just one season at Wolves, Nunes left the club in the summer of 2023 to sign for Manchester City in a £53million deal as Pep Guardiola looked to regenerate his midfield following their treble-winning season.

Signing with Ilkay Gundogan leaving the club for Barcelona, Nunes would’ve hoped to feature more than he did. 31 appearances in all competitions doesn’t sound too bad, but the reality is he played just over 1500 minutes across all competitions and just over 800 in the Premier League, making just nine starts.

A year on and City have re-signed Gundogan for free, meaning the Portuguese midfielder is once again even further down the pecking order. Quietly a rather poor piece of business.

Michael Owen – Real Madrid to Newcastle

In a bid to better his chances of making the 2006 World Cup squad, Owen returned to England looking for more regular minutes, swapping Real Madrid for Newcastle in the summer of 2005 for a club-record £16.8million.

The striker started well, but broke his metatarsal bone in December and didn’t return to the pitch until April 2006. He then missed the final game of the season, went to the World Cup and suffered an ACL injury, which kept him out of action until April 2007.

Owen was never able to recover after that string of injuries and his form declined as well as his availability. He signed for Manchester United upon the expire of his Newcastle contract in 2009, having managed 23 goals across his final two seasons at the club from 2007 to 2009.