With rolling media coverage dialling up the drama as clubs race against the clock to get deals over the line, it has become one of the most eagerly anticipated days in the football calendar.
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But for players it can be a day to endure rather than enjoy, with the tension rising as the clock ticks towards the deadline.
That was the case for Shaun Goater in March 1998, when it felt like time and technology were against him as he waited nervously to seal his move to Manchester City from Bristol City.
“This was my dream move – a big club, I wanted this to happen,” he recalled on the most recent instalment of the We’re Not Really Here matchday show.
“It’s ten to five and we’re sending the response back through a fax machine and it gets jammed. My wife tells me to get out the way and unjams it. She sends it.
“It’s two minutes past five and I’m just thinking it’s not going to happen. I was really nervous as to whether or not it was going to go through. It was a scary thing.
“City had come in late, which left me with the best part of an hour to read through the contract, sign it and send it back. I was still reading and signing it as I was sending the fax!”
Richard Dunne sympathises with his former team-mate.
The one-time City captain says players usually have a good idea of whether they’ll be leaving on deadline day and which club will be their destination, but when the deal will actually be completed can be anyone’s guess.
That was the case for Dunne in August 2009, when the window had closed and he remained unaware of whether or not his move from City to Aston Villa had gone through in time.
“The deadline was 5pm and I remember leaving the training ground at Aston Villa at ten past five and Sky Sports were outside saying congratulations and asking if I’d signed,” he explained.
“I said: ‘I haven’t got a clue,’ because at ten past five nothing had been confirmed. The fax machine wasn’t on or whatever it was and you’re waiting for a response.
“Generally, you will have an idea three or four days leading into it and it might take until deadline day. When it gets down to the last few minutes, then it is a bit of a worry and a stress.”
It got more bizarre for Dunne three years later when a move away from Villa was on the cards.
Malaga were the interested party, but the transfer that never materialised is a tale of how deadline day can take footballers to the must unusual locations.
“I came back from the Euros in 2012 and I was injured and I’d got speaking to Malaga about going on loan,” added the 41-year-old.
“On deadline day I remember being in TGI Friday’s all day with my passport just waiting to go.
“Late that night they put an offer in and I got a phone call saying ‘we’ve had an offer from Malaga, but it’s in Spanish and we don’t know what it says.’”