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Transfer Deadline Day: The best deals and biggest winners

Updated: Mar 7, 2020

As the Summer 2019 Transfer Window slammed shut in England, I take look at the biggest deals on Deadline Day. Who were the main winners and losers?

I've always loved Transfer Deadline Day. It's become a yearly ritual to be glued to Sky Sports News as presenters speculate over who will go where and which clubs will splash the cash.

Last season they moved the Deadline Day forward to ensure all business was done on the eve of the new season, and this year was no different. Sounds sensible to me. This view was confirmed earlier when I read the seethe coming from former Sky Sports presenter Richard Keys that Premier League teams were being disadvantaged as a result.

Cheque books have been hidden away again for another few months, but which clubs were the main players this Deadline Day?


Let’s start with Arsenal. Having signed Lille winger Nicolas Pepe for a club record £72 million last week, Deadline Day was another busy one of spending for the Gunners.

After a long summer of negotiation, Arsenal finally got their man. That man of course being Celtic left back Kieran Tierney for the price £25 million. Some Arsenal fans were sceptical at the large free (especially when they were told they 'only' had £45 million to spend...), but at the age of 22, Tierney has won three domestic trebles at Celtic, has two Champions Leagues campaigns under his belt and a winning mentality (albeit from Scotland).

There is two trains of thought on Tierney. The first one is that he'll be as successful as fellow countryman Andy Robertson and take the league by the storm, the other being that he's too injury prone and also relatively untested. I suppose time will tell with that one.

In one of the shock moves of the summer, Arsenal also landed Chelsea’s Brazillian defender David Luiz for the bargain price of £8 million. Luiz went on strike to force the move through and there’s never a dull moment with this attack minded defender in your team. Most surprising deal of the summer? Could well be. Luiz is a winner and an absolute steal.

Tottenham Hotspur

The final 24 hours of the Transfer Window must've been an emotional rollercoaster for Spurs fans. Firstly a loan move for Barcelona’s Philip Coutinho fell through before a £65 million deal for Juventus attacker Paolo Dybala followed in similar vein.

Such disappointment was quickly masked with the signing of Fulham's hotly tipped 19 year old left wingback Ryan Sessegnon for a deal worth £25 million. Sessegnon has already played over 100 games for Fulham and was featured in the 2017/18 Championship Team of the Season. He may not have replicated that success last season, but he still managed 35 Premier League appearances. Not bad for a teenager. Danny Rose has some serious competition for that left back spot.

Mauricio Pochettinho was also able to persuade 23 year old fellow countryman Giovani Lo Celso to sign a year long loan from Real Betis. The 19 timed capped Argentinian midfielder is expected to sign a permanent deal next summer for a fee of £55 million, a pretty decent bit of business all things considered. Spurs should be close to challenging again this coming season, and it’s good to see Daniel Levy finally loosening the purse strings! New signings, new stadium and Poch is staying, happy days for Spurs fans.


The Toffees have had a brilliant summer of recruitment and, despite failing to land Wilfred Zaha from Crystal Palace (and saving themselves a pretty penny in the meantime), they still managed to sign Alex Iwobi from Arsenal for £28 million (potentially rising to £34 million). He scored 3 goals and assisted 7 last season in 35 matches for Arsenal but with Pepe’s arrival, it looked like his opportunities were limited. I always felt underwhelmed by Iwobi at Arsenal if truth be told, but he may thrive at a different club.

Everton have had a brilliant window so far, managing to lure Italian teenage sensation Moise Kean from Juventus for £29 million. The 19 year old is already the youngest ever player to score for Italy and it was a shock that The Old Lady didn’t try harder to keep him. Juve's loss is definitely Everton's gain. Kean was the first name in my Fantasy Football team so I'm praying he'll set the grass on fire this season.

Man Utd

This one should be stored under ‘lack of transfer activity’, very much to the frustration of their fan base. There appeared to be a resignation to a big name signing come Deadline Day and even Pizza Hut had a wee dig at their expense on Twitter!

Romelu Lukaku really didn’t want to return to Old Trafford for pre season and his forced move away from the club was confirmed with a £74 million deal to Inter Milan. Harry Maguire and young right back Aaron Wan-Bissaka may have strengthened their back line, but the failure to sign a new striker (and/or big name) could come back to haunt them. I have a sneaky feeling that it's not going to be a happy season for the Red Devils.

Deals for Paolo Dybala, Christian Eriksen, Inaki Williams and Mario Mandukic all fell through and you have to wonder how they can see themselves as genuine contenders for the top four, never mind the Premier League trophy. If Zidane pushes the boat out and takes Paul Pogba to Real Madrid (as is heavily rumoured), Man Utd could be in for a long season of discontent.

Other main deals on deadline day

Andy Carroll rejoined his boyhood club Newcastle on a one year deal on a free on the final day. England goalkeeper Scott Carson joined Man City on a year long loan in a bizarre move from Derby and Swiss international Striker Albian Ajeti joined West Ham for £8 million from Basel. Still only 22, Ajeti scored 29 goals in 58 league games for Basel and is definitely one to look out for.


Big winner - It has to be Arsenal. I’m really excited to see how Kieran Tierney and David Luiz get on at the Emirates this season as they seek a top four place once again. I have a feeling they'll pip Man Utd and Chelsea (especially with their transfer ban) to that spot.

Biggest disappointment - Man Utd. You could argue Liverpool fans will be disappointed at their club for not strengthening, but with the best front line in the Premier League, 97 points last season and a Champions League trophy sitting in the Anfield trophy cabinet, you’ll forgive them for not complaining too much. Man Utd on the other hand have lost a proven Premier League goalscorer and have failed to lure a lot of big names to the club.

Arsenal and Spurs fans will have a spring in their step going into the new season but I was disappointed at the lack of 'wow' signings this Transfer Deadline day. We really could've done with a Tevez to West Ham (2006) or a Robinho to Man City (2008) type signing! It really is what it is.

All in all, the Transfer Window has set up the Premier League season for another intriguing year. My money is still on Man City.


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