Transfer Deadline Day has often been one of the most anticipated days on the football calendar, a time in which has produced some unforgettable Premier League tales.
From the shocking to the utterly bizarre, almost anything is possible on deadline day and we’ve decided to revisit some of the most memorable moments from Transfer Deadline Day of years gone by.
Five unforgettable Transfer Deadline Day stories:
Redknapp packs Benjani’s bags
Harry Redknapp is a Deadline Day icon. From his famous car window interviews to late deals for old favourites, Redknapp was rarely far from the headlines when it came to transfer talk.
One of his most compelling Deadline Day tales came in February 2008, when Redknapp took the rare action of pushing his star striker out of the exit door. Benjani had scored an impressive 12 goals in 23 appearances for Portsmouth across the first half of the season, but Redknapp believed an offer from Manchester City was too good to refuse.
“Out of the blue I get an offer from Manchester City of around £9.5m, and no disrespect to Benji, I really did not expect to get offered £9m for him,” he told talkSPORT.
“Someone at Man City told me he hadn’t got on the plane!” ✈️
— talkSPORT Breakfast (@TSBreakfast) August 9, 2018
“I told Benji he is going to Manchester City, how it is a great move for him, and he should go, but he said ‘I like it here gaffer, I don’t really want to move’.
“Eventually I got him to the airport, then suddenly I get a phone call from Manchester saying he has not arrived on that plane. I went to the airport and eventually I find him, I say ‘you’re supposed to be in Manchester Benji’ and then suddenly there is one more late plane, but he don’t want to go.”
“I end up dragging him across the runway pushing him, telling him he should go,” Redknapp continued.
“He was getting towards the departure gate and he was telling me he wants to stay at Portsmouth, I ended up pushing him and getting him onto the plane – it was about half past twelve by the time he got there.
“He was a fantastic boy, but it was a fantastic deal, and I had to push him onto the plane to get him to go and do it.”
Ryan Babel was involved in one of the most peculiar Deadline Day tales in August 2010, with mystery continuing to surround his helicopter ride to London.
Babel had fallen out of favour under Rafael Benitez at Liverpool and was subject of interest from West Ham, as the two clubs discussed a swap-deal that would have involved Carlton Cole heading to Anfield.
Babel was reported to have been spotted boarding his transport for talks with the Hammers, but never arrived in London and the helicopter was never confirmed to have landed. Its journey remains a mystery and the tale of the Babelcopter was born. The Dutchman later revealed insight into why he snubbed the switch.
“I was at one point very close to joining West Ham,” he told the Liverpool ECHO. “It was supposed to be a swap deal for Carlton Cole at one point. However, it didn’t go to plan.
“I was told that it was supposed to be a loan deal until the end of the season, and then I will come back to Liverpool. But on deadline day, I came to figure out that West Ham was going to buy me and I wasn’t willing to do that.
“Also my agent wasn’t aware or was briefed wrongly. So in the end, my agent and I decided not to do it and the transfer didn’t happen.”
Torres, Suarez, Carroll and chaos
Has there ever been a Deadline Day quite like January 2011?
The final stages of the winter window saw a memorable merry go round of centre-forward signings, as Liverpool and Chelsea spent big on firepower. There was a feeling of optimism at Anfield after Fenway Sports Group had saved the club from the ownership of Tom Hicks and George Gillett, while club icon Kenny Dalglish has returned for a second spell as manager.
Liverpool, however, faced a fight to hold onto the services of Fernando Torres. El Nino had shone across three-and-a-half seasons with the club, in which he scored 81 goals in just 142 appearances. Interest from Chelsea – keen to reignite their season – had turned Torres’ head and the Spaniard slapped in a transfer request amid interest from west London.
12 years since one of the wildest deadline days in Premier League history…
➡️ Suarez & Carroll (Combined £58m)
⬅️ Fernando Torres (£50m) pic.twitter.com/3zjS3kP9Sy
— The Anfield Wrap (@TheAnfieldWrap) January 31, 2023
Liverpool had hoped to pair Torres with Luis Suarez, who was on the verge of completing his move to the Premier League from Ajax. What followed instead was a remarkable Deadline Day, as Liverpool launched a move for Newcastle’s Andy Carroll ahead of Torres’ expected exit.
The Reds’ desperation drove up the fee for the giant Geordie, who became the most expensive British footballer of all time at £35m. Carroll had scored just 14 goals in the Premier League, but was now on his way to Merseyside in a club-record deal.
As Carroll’s helicopter headed to Liverpool, Torres travelled to the capital. The deals for Carroll and Suarez were announced before the deadline, but there was a nervous wait for Chelsea as Torres’ transfer was confirmed 20 minutes after the window shut – for a British record £50m. David Luiz also joined in a late dash for new recruits at Stamford Bridge, with more than £134.2 spent by the two clubs in the final hours. At that time, the numbers were absurd.
Odemwingie takes the wheel
Peter Odemwingie, quite literally, looked to steer his career in a new direction in January 2013.
The Nigeria international’s infamous drive to Loftus Road has become Deadline Day folklore, with the then-West Brom forward making the drive south in the belief he was on the verge of completing a move to Queens Park Rangers.
QPR wanted to sign Odemwingie to boost their battle against relegation, but the deal collapsed. Odemwingie was forced into an embarrassing situation, left outside Loftus Road in his car and refused entry into the ground after both clubs insisted a fee had not been agreed.
— Sky Sports Retro (@SkySportsRetro) October 5, 2020
Odemwingie later revealed that Junior Hoilett’s refusal to move to West Brom as part of the deal saw his transfer collapse.
“Everything seemed agreed, but actually I didn’t know that one of the terms was that they [West Brom] were getting [Junior] Hoilett and [if I had known that] I would have never driven to London,” Odemwingie told Sky Sports.
“Why would I have driven to London in bad weather? It was dark already, it was winter and I had just had a new born, who was one week old.
“One thing I would have done [if I had known] is call my friends at QPR and say ‘hey guys, can you find out whether Hoilett will actually come to West Brom or not?’
“That’s what I would have done. But I didn’t have to because I thought it was never a condition that he had to go the other way.
“I was left there waiting for the agents to tell me what’s next. Then the time was ticking, I had a medical to go through, I obviously had to read the contracts and everything had to be drafted.”
Faulty fax machine
Technology issues were blamed for the failure of a swap-deal between Real Madrid and Manchester United in 2015, when a fax machine glitch played its part in a collapsed transfer.
The two teams were in talks over a goalkeeping trade that would have seen David de Gea head to the Spanish giants, with Keylor Navas signing for Manchester United in exchange.
A farcical failed transfer followed, as both clubs attempted to shift the blame on who had failed to sign the required paperwork in time. United were initially blamed with a faulty fax machine the issue, as Real Madrid missed the 10pm deadline to register De Gea and the goalkeeper remained at Old Trafford.
🎞 Remembering the broken Fax Machine as David De Gea’s transfer from Manchester United to Real Madrid never happened. pic.twitter.com/RkjiKhVPyo
— Football Daily (@footballdaily) September 1, 2022
United released a statement in which the club claimed proof of conducting their half of the transfer in time, but equally created suspicion after expressing their ‘delight’ that De Gea would be staying at the club.
Football’s transfer dealings, in an overdue move, has since moved on from fax machines to avoid a repeat.