10. Wayne Bridge (loan from Manchester City)
When Martin O'Neill made Wayne Bridge his first signing as Sunderland manager it was one met with optimism from our fans, with the hope being that Bridge would resurrect what had been a fledgling career at Manchester City whilst a Sunderland player.
Bridge's direct competition for the starting berth at left back was Kieran Richardson, and sadly for both him and the Sunderland fans he struggled to dislodge the ex-Manchester United man between January and the end of the season, starting only three Premier League games before returning to his parent club in the summer.
The version of Wayne Bridge Sunderland received wasn't the one that had amassed almost twenty million quid in transfer fees and played thirty-six times for England, but the version that had grown largely disillusioned with the game having spent alot of time on the bench and in the treatment room. Never mind.
9. Rory Delap (free transfer)
Before joining Sunderland, Delap had earned a reputation as a solid utility man at both Derby County and Southampton in the Premier League, and when the opportunity to bring him to the club on deadline day of 2006 arose he was quickly snapped up by Mick McCarthy.
Delap was thrust straight into the first team at Sunderland. and after a handful of games he had his nose accidentally broken by George McCartney and was ruled out for the season. By the time the start of the next season came around he was deemed surplus to requirements by Roy Keane and was allowed to join Stoke on loan, where he rather bizarrely was allowed to play just a week later against us, his parent club, and was unfortunately injured by a tackle from Clive Clarke which smashed his leg to bits and ruled him out for the rest of that campaign. Yep.
Despite all of that it didn't deter Tony Pulis from signing Delap on a permanent basis and, well, the rest is history - from there the Irish international managed to carve out a fairly impressive Premier League career with Stoke as a long-throw specialist, with many believing that his throwing technique was the reason why The Potters stayed in the top flight that season. Strange, really, as it took until 2007 for someone to realise just how handy he was.
8. Stanislav Varga (£0.5m from Celtic)
Sunderland fans often regale the 2006 summer transfer window deadline day under Roy Keane with relative joy, earmarking it as the day which remarkably changed the future of our football club. In signing names such as Dwight Yorke, Graham Kavanagh and David Connolly - just three of six players signed on that fateful day - Sunderland and Roy Keane were flexing their muscles, backed by the Drumaville consortium, and had announced to the world that this was a club with ambitions far exceeding the Championship.
It would have been easy to lose him in the shuffle, but also signed on that day was Stan Varga, a player already familiar to Sunderland fans having spent three years at the turn of the millennium at the club as a backup central defender.
Having enjoyed possibly the greatest debut ever by a Sunderland player, in a game which saw him keep quiet one of the best of all time in Thierry Henry, it was all downhill from there for big Stan and he was eventually released in January 2003, allowing him to leave to join Celtic. It was at the Glasgow club where he enjoyed a revival of sorts, becoming a regular under Martin O'Neill as Celtic marched on to win two Scottish league titles with Varga at the heart of their defence.
Varga's return to the club in 2006 was as underwhelming as his first spell, and having found himself behind Nyron Nosworthy in the starting eleven he was released in the summer of 2008. Of the six players signed by Keane on that day, Varga was most definitely the worst.
7. Sotirios Kyrgiakos (loan from Wolfsburg)
Having signed on loan from Wolfsburg on January deadline day in 2012 it was almost two months until he actually played under Martin O'Neill, brought into the side as injuries to John O'Shea and Wes Brown saw Kyrgiakos play as part of the side that disappointingly lost away to Blackburn Rovers, a team that went on to be relegated that season.
Liverpool fans told us when he signed that he was crap and, well, he was. We probably should have listened to them.
Kyrgiakos was only on the winning side once while at Sunderland - a home victory against Queens Park Rangers - and was used sparingly before returning to his parent club at the completion of the season. He was one of many bizarre Martin O'Neill loan signings that didn't really make sense, and really wasn't worth the bother of having to google his name every time you wanted to talk about him.
6. Andrea Dossena (free transfer)
Having been given the remit that Sunderland were desperate for a left back, Roberto De Fanti signed this absolute knacker on deadline day in the summer of 2014.
Although he looked decent on his debut against Newcastle, he was sent off for an absolutely horrific tackle on David Meyler a week later away to Hull that probably should have seen his contract torn up there and then.
The less said about him the better.
5. Ricky Alvarez (loan from Internazionale)
If Sunderland had a Director of Hindsight in the summer of 2014 he might have strongly advised Sunderland to give the signing of Ricardo Alvarez a wide berth. Due to no fault of his own the transpiration of his arrival on Wearside has caused the club no end of problems and still, to this day, we find ourselves bound in legal action regarding who is financially responsible for Alvarez.
The Argentina international came to the club with a glowing reputation, but unbeknownst to us he arrived here with an underlying knee injury which meant he started only five league games all season.
That was just the start of Sunderland's issues with Alvarez - upon the completion of last season the player found himself in the middle of a contractual wrangle between his parent club, Inter, and us, culminating in a tonne of legal action which, as I type, is still going on.
Alvarez played his first game of the season at the weekend for Sampdoria, with FIFA allowing the Italian club special dispensation to sign Alvarez on a free transfer, ruling that it's unfair on the player that he should be made to wait until Sunderland and Inter figure out just who owns him. Fair enough, I suppose. I bet we wish we had never bothered.
4. George McCartney (£8m from West Ham United)
Sell a player for buttons, don't replace him, then two years later buy him back from the club you sold him to for an inflated fee on deadline day because you really need a player in that position, having never properly replaced him in the first instance.
The most Sunderland thing ever.
3. Benjani Mwaruwari (loan from Manchester City)
He’s a big, strong, powerful centre-forward and one we’ve been tracking for a long time. I’m delighted that we’ve been able to bring him to the club.
He’ll bring another dimension to our striking options and will be a great addition to the squad.
Actual words that left Steve Bruce's mouth.
Mind, it wasn't the most hilarious thing about the whole Benjani affair. I'm not sure what was worse, the fact our fax machine broke and we had to get special dispensation from the FA in order to complete the signing, or the fact his only contribution whilst a Sunderland player was a deflected shot that fell to Darren Bent's feet in a home win over Birmingham City. Awful player, and an awful transfer that made absolutely no sense back then and still makes absolutely no sense now.
2. Danny Graham (£5m from Swansea City)
Perhaps the worst signing that Martin O'Neill made was Danny Graham, and despite arriving on the back on a fairly positive spell at Swansea it was another head-scratcher that could have been avoided if we had a Director of Hindsight.
In twenty-two league starts he scored just once, a shot from Jermain Defoe that deflected in off his arse last season away to Everton. That just about sums up his time at Sunderland, really.
I'm sure he was a nice lad, and he always worked hard when he played for us, but he just wasn't good enough at this level. Now he's on loan at Blackburn until the end of the season we have likely seen the last of Danny Graham in a Sunderland shirt.
1. Tore Andre Flo (£6.75m from Glasgow Rangers)
The quest to replace Niall Quinn was never going to be an easy one, yet electing to throw almost seven million quid on deadline day at Rangers for a player that wasn't even playing well in the Scottish league has to rank as the worst piece of transfer business in the history of Sunderland AFC.
It was almost as though Peter Reid had never watched him play. Although Flo was tall, he wasn't particularly known for his aerial ability, and having been brought in to basically win long balls and feed them to Kevin Phillips he struggled massively. Despite scoring on his debut for the club, against Manchester United, it was clear from the very beginning that Reid had made a massive error in purchasing Flo - the shining example of a panic buy if ever there was one.
Not only was Flo not particularly good but he was unfit, and he rarely lasted a full game which became a tactical nightmare for a team that were inevitably relegated at the end of the season. Had the funds used to sign Flo been utilised better in the seasons prior, Sunderland would have almost certainly been a stable top ten club. Instead, we found ourselves in division one, riddled with debts and players on obscene wages that we just couldn't move on.
It was a mess which inevitably led to Bob Murray selling the club just a few years later, and the money spent on Flo was seen by many as the final straw in the tenure of Murray as Chairman.
Which of the ten do you think was the worst deadline day signing? Vote in the poll below!