The Worst Ever Deadline Day Deals (Top 10)

The Worst Ever Deadline Day Deals (Top 10)

Deadline Day is once again upon us, with players and clubs scrambling to make those last-minute moves. From transfer sagas that have lasted weeks, to deals appearing out of thin air, there’s carnage and chaos everywhere you look.

Despite there being some memorable moments on deadline day in recent years, there has also been a fair number of shocking deals that have made it over the line. Football Park looks at the top 10 worst deals in transfer deadline day history.

10 - Andre Santos (Fenerbahçe to Arsenal, 2011)

Andre Santos had the potential to the be full-back Arsenal manager Arsene Wenger wanted him to be, as he proved at Fenerbahçe he had the quality and ability to thrive under his new boss.

Santos made 78 appearances for the Turkish side, scoring 17 goals and recording five assists. The Brazilian’s attacking nature added an extra string to his bow, making Santos a well-rounded full-back. The Gunners signed Santos for £6.2m, however his time with the club was spent stuck in second gear.

The left-back only made 33 appearances for Arsenal, scoring three times for the Gunners. Santos spent one and a half years at the club, unable to solidify his spot within the team.

Ultimately Arsenal sent the Brazilian out on loan to his home country to play for Gremio, before deciding not to give Santos a new deal when his contract expired. He went on to join Flamengo where he managed to enjoy a successful spell with the club.

14 years ago today, Arsenal signed FIVE players on Deadline Day

Mikel Arteta
Per Mertesacker
Andre Santos
Chu-Young Park
Yossi Benayoun

4 of these players would play a huge role, as Arsenal made a miraculous late recovery that season to qualify for the Champions League. pic.twitter.com/5g7IyWM1jI

— ابو (@MAA_Gunner) August 31, 2025

9 - Xisco (Deportivo La Coruna to Newcastle, 2008)

Newcastle felt it was necessary to add to their six forwards already in their strike force, and signed Xisco from Deportivo La Coruna for £5.7m. The Spanish international had impressed at his former club, accumulating 20 goals contributions in 75 games.

The Magpies unsurprisingly didn’t give Xisco many appearances as he only played 11 matches for the Premier League outfit. The striker only scored one goal and provided one assist during his time at the club. Loan spells to Racing Santander and former club Deportivo La Coruna were sandwiched in between his appearances for Newcastle.

Xisco left Newcastle after his contract was terminated in January 2013, with the forward’s signature being a strange transfer before he had even kicked a ball for the Magpies.

Xisco - Deportivo La Coruña to Newcastle United (2008) pic.twitter.com/9sfyRrDZjJ

— Transfersthathappened (@actualtransfers) September 11, 2023

8 - Paul Konchesky (Fulham to Liverpool, 2010)

When Roy Hodgson was manager of Fulham he was a massive fan of Paul Konchesky. Therefore it was no surprise that the former England manager had the full-back on his radar once he was the head coach of Liverpool.

After making 122 appearances for Fulham, which included nine goal involvements, Konchesky signed for the Reds in 2010 for £4m. However the left-back struggled to ignite his Liverpool career, playing only 18 games for the club.

This could be down to the fact that Hodgson was no longer the manager by the start of January, as Kenny Dalglish had replaced the former Liverpool boss. Konchesky was then sent out on loan to Nottingham Forest for the remainder of the season, before making a permanent move to Leicester City.

#OTD in 2011:
After a terrible year at Anfield, Paul Konchesky joins Leicester having made just 18 Liverpool appearances pic.twitter.com/AZ3rMw68ha

— Liverpool On This Day (@OnThisDayReds) July 13, 2024

7 - Afonso Alves (Heerenveen to Middlesbrough, 2008)

Middlesbrough went all out for striker Afonso Alves as they broke the club’s transfer record in order to sign him. For his previous club Heerenveen, Alves scored 45 goals in 38 appearances and looked to be a great signing for Boro manager Gareth Southgate.

However during his time with Middlesbrough the Brazilian only netted 10 goals in 42 games. Half of these goals came across the span of two games, against both Manchester clubs.

Alves scored three goals against Manchester City in an 8-1 win for Middlesbrough in May 2008. A few weeks prior to that game, the striker scored a brace against Manchester United in a game that ended in a 2-2 draw.

Alves never lived up to the hype and expectation when he signed for Boro, and departed the club in 2009 after Middlesbrough were relegated to the Championship.

🗓️ On this day in 2008, A hat-trick from Afonso Alves helped Middlesbrough beat Manchester City 8-1. pic.twitter.com/i2N2usy78b

— Football Talk (@FootballTalkHQ) May 11, 2023

6 - Benni McCarthy (Blackburn to West Ham, 2010)

Benni McCarthy enjoyed a successful four-year stint with Blackburn before joining West Ham. The forward had scored 52 goals in 140 appearances for the Rovers, which attracted the interest of the current Hammers boss Gianfranco Zola.

The London based club secured the signature of McCarthy for £2.5m, who had shown the signs of being a prolific striker during his time at the Riversiders. However the South African international failed to score for the Hammers and only made 14 appearances for the club.

An absolute nightmare for both parties, as McCarthy never managed to find his shooting boots he once had at Blackburn. After being regularly left on the substitutes bench and not included the matchday squad, McCarthy’s contract, which still had 14 months left, was terminated for £1.5m.

=2315. Benedict "Benni" McCARTHY

Forward - 12.11.77 - SAF (79/31)

Prem Debut:
19/08/2006 (Portsmouth vs. BLACKBURN ROVERS, L 3-0)

Prem Clubs:
Blackburn Rovers (06-10), West Ham United (10-11)

Prem Apps: 120
Prem Goals: 37 pic.twitter.com/I4Q6VmXygc

— Premier League Players (@premlgeplayers) January 30, 2024

5 - Robinho (Real Madrid to Manchester City, 2008)

With Manchester City having just been taken over by Sheikh Mansour, the club wanted to announce to the world what a financial powerhouse they were. That’s where the signing of Robinho comes in, as the Citizens signed the Brazilian international for £32.5m.

Robinho was all set to join Chelsea, however on deadline day the saga took a twist as the Blues released pictures of Robinho shirts on their club website. Real Madrid didn’t take nicely to this which led to the deal falling through. For what was Chelsea’s pain was Manchester City’s pleasure as they swooped in to sign the Brazilian.

However a confused Robinho thought that he was signing for Manchester United after not realising that Manchester City existed.

His time with the Citizens was a failure, as the winger scored only 14 goals in 41 Premier League appearances. The Brazilian left the Manchester based side two years later, moving to AC Milan.

Thirteen years ago, Robinho joined Manchester City. His reason for signing remains unforgettable:

"Yes, I thought I was joining Manchester United. I was misled by all involved. I wasn't aware there was another Manchester club."

😂😂😂 pic.twitter.com/nmaIRGQM8J

— Footy Humour (@FootyHumour) July 17, 2024

4 - Radamel Falcao (Monaco to Manchester United, 2014)

Radamel Falcao joined a star-studded lineup of attackers in Manchester United’s team during the 2014/15 Premier League season. The striker joined the Red Devils on a season long loan worth £6m, with an option to make the deal permanent for £43.5m. The Colombian partnered up with the likes of Wayne Rooney, Robin van Persie and Angel Di Maria in a strike force that looked set to terrorise defences.

However as with the case of Manchester United over recent years, Falcao’s addition to the squad turned out to be a huge failure. The forward only made 29 appearances across all competitions and scored just four goals.

His loan move was understandably not made permanent and instead spent the following season at Chelsea. Yet another example of how United try to strengthen in positions that aren’t the priority at the time.

Radamel Falcao (28)- AS Monaco to Manchester United on loan (2014) pic.twitter.com/FZDYRmO8a6

— Transfersthathappened (@actualtransfers) June 9, 2025

3 - Andy Carroll (Newcastle to Liverpool, 2011)

Andy Carroll earnt a move to Liverpool after impressing with boyhood club Newcastle United. In the 2010/11 Premier League season the striker scored 11 goals and recorded eight assists in just 19 top flight appearances.

That attracted the attention of Liverpool, who swooped in to sign the 6ft 4in forward for £35m. He inherited the No.9 shirt, which was left in the wake of Fernando Torres leaving to join Chelsea.

Despite spending just over two years with the Reds, Carroll only made 58 appearances and scored just 11 goals. A number of factors were to blame for this, including a mixture of injuries and poor form that limited his game time.

These were the ingredients that ultimately terminated his time at the Merseyside club, as the England international was moved out on loan to West Ham only two games into the 2012/23 campaign.

Andy Carroll (22) (€41M) - Newcastle United to Liverpool (2011) pic.twitter.com/7BNvKLUP8Q

— Transfersthathappened (@actualtransfers) June 15, 2025

2 - Antony (Ajax to Manchester United, 2022)

Antony was one of the many players that made the move from Ajax to Manchester United, as Erik ten Hag looked to bring over his star players from the Dutch club. The Brazilian international set United back £82m and hasn’t come anywhere close to justifying that price tag.

Antony made 96 appearances for the Red Devils, scoring just 12 goals and assisting five more. To put that into perspective, during his loan move to Real Betis the winger scored nine goals and assisted five more in just 26 games. So in 70 more appearances for United than Betis, Antony only scored three more goals.

The former Ajax player has now left Manchester United after making a permanent transfer to Real Betis, with the Spanish club paying £21.7m for the player. A loss of £60.3m highlights one of the many problems with United’s transfer business over the last decade.

Antony is returning to Real Betis after sealing a permanent transfer away from Manchester United.

Antony in 96 Manchester United games: 17 G/A

Antony in 26 Real Betis games: 14 G/A

😏 pic.twitter.com/W66HNXlPjg

— B/R Football (@brfootball) September 1, 2025

1 - Fernando Torres (Liverpool to Chelsea, 2011)

Fernando Torres enjoyed himself during his time at Liverpool, showing the world that he could make it in the biggest league in the world. His debut season with the club during the 2007/08 campaign saw the striker score 24 league goals in 33 Premier League games.

However towards the end of his stint with the Reds the Spaniard faced injury and confidence problems. These issues remained prominent when he moved to Chelsea for £51.5m in 2011, as Torres didn’t hit the ground running by any stretch of the imagination.

His debut for the Blues ended in a 1-0 defeat to Liverpool, an ironic moment which would foreshadow his tenure with the London based club. A 903-minute goal drought ensued which lasted two months, until it was broken by his only goal of that season.

In his following campaigns with Chelsea Torres failed to find any form, scoring only 45 goals in 172 appearances for the club. The Blues then sold the forward to AC Milan in 2014, ending the horror show of their four-year partnership.

Fernando Torres joined Chelsea for £50m, and in 110 apps, he's managed 20 goals. pic.twitter.com/foZdTSUO2i

— Rubbish Transfers (@RubbishTransfe) July 20, 2014