Historically, the January transfer window has not been one in which Tottenham Hotspur have particularly done their best business in.
Recent times may suggest otherwise, with the likes of Dejan Kulusevski, Rodrigo Bentancur and Pedro Porro all examples of how Spurs have been able to strengthen their squad during the winter window.
The Lilywhites will have a huge opportunity this winter to replenish Ange Posteocglou's side with injuries and international tournaments set to deplete the Australian's options over the next month.
The top 10 Tottenham Hotspur January signings – ranked
With Spurs looking to do business in the winter window, we have looked back at Tottenham Hotspur’s best January signings.
ByBrogan Clasper
However, it certainly hasn't always been as easy for Spurs to nail their recruitment during the month of January and we at Football FanCast have taken a look at the times in which Spurs have got their January spending wrong.
10 Lewis Holtby January 2013
The German midfielder may have won some fans over during his time in north London after making the move from Schalke in 2013, however, his time on the pitch failed to deliver.
His 25 appearances in the Premier League mainly came off the bench and he was only able to provide the Lilywhites with one goal and two assists in that time (via Transfermarkt).
Fortunately for Spurs, they did not pay huge money for Holtby as they certainly did not see a return on the pitch. However, they did see a tidy return in 2015 after his loan move to Hamburg SV was made permanent and they made a considerable profit on the German.
9 Steven Pienaar January 2011
This is by no means the worst piece of transfer business done by Tottenham in the January window, but it is nowhere near some of their best work.
In signing the South African, Spurs were bringing in a player who had considerable Premier League experience following his time at Everton.
However, that means the club will be aware that he was never destined to pull up any trees in north London given his fairly tame returns in the Premier League with the Toffees (via Transfermarkt).
Anyway, 18 appearances, one goal and two assists later for Spurs, Pienaar made his return to Goodison Park and – like with Lewis Holtby – Spurs managed to turn a profit.
8 Zeki Fryers January 2013
Tottenham may have thought they were about to unearth a gem when they brought Zeki Fryers back to England from Standard Liege following his time as a youngster at Manchester United.
However, this was certainly not a transfer which benefited Tottenham. The English defender went on to make more appearances for Tottenham's U21s side (23) than he did for the first team (15).
And only seven of those appearances for the first team came in the Premier League before he was then sold to Crystal Palace in 2014.
Perhaps the saving grace for Fryers not being any higher on this list is that Spurs were – somehow – able to turn a small profit on the defender when he made the move to the Eagles.
7 Gilberto January 2008
In the 2008 winter window, Juande Ramos made a number of signings with the likes of Alan Hutton and Jonathan Woodgate coming through the doors in north London.
Alongside the defensive duo was the left-back, Gilberto. However, his time at Spurs will not be remembered so fondly.
The Brazilian was only able to total 10 appearances for the club over the one-and-a-half seasons he spent with the club. Adding to his lack of appearances, the defender was allowed to leave the club on a free in 2009 when his contract expired in a return to Brazil with Cruziero.
Having provided an impressive return of 15 goals and 16 assists during his time with Hertha Berlin, this proved to be a seriously underwhelming signing.
6 Mounir El Hamdaoui January 2005
Who, you may ask? Well, the Moroccan forward joined Tottenham in January 2005 as a 20-year-old from Dutch Eredivisie side SBV Excelsior.
Having impressed in training and a friendly game for Spurs, Martin Jol's side signed the youngster, but he did not go on to play another game for the Lilywhites.
Indeed, after just a matter of months at the club, El Hamdaoui was then sent out on loan to Derby County before eventually being let go by Tottenham in a free transfer to Willem II the following summer.
5 Bongani Khumalo January 2011
Agreeing to join from South African side SuperSport United in October 2010 for over £1m, the defender's time in north London was a huge failure as he, ultimately, spent his time away from Spurs over five separate loan deals.
Khumalo was bought just a matter of months following his displays for his national side when they hosted the 2010 World Cup, but it was not a move which provided the Lilywhites much.
In fact, the South African centre-back did not play once for the first team during his time in north London and he did not even really feature for the U21s side with just seven appearances to his name for them (via Transfermarkt).
Five years after he left SuperSport United, Khumalo returned to the South African side after his contract came to an end at Spurs and the Lilywhites were forced to cut their losses as he returned to his former club on a free.
A truly disastrous buy from Tottenham.
4 Gedson Fernandes January 2020
Yes, this is a name which Spurs fans will remember vividly as the Portuguese midfielder only arrived at the club back in 2020 – the same window as Bergwijn.
He joined on an initial 18-month loan deal from Benfica which had the option to be made permanent for a staggering fee of £42.76m.
Spurs were even able to beat their London rivals, West Ham United, to the signing of Fernandes after the midfielder chose the Lilywhites over the Irons.
But it is perhaps the Hammer who had the last laugh in this case with Fernandes proving to be a disastrous arrival in north London.
Over his time with the Portuguese star only made 14 appearances across all competitions where he only racked up 445 minutes of football; as a result, Benfica recalled their midfielder after 12 months.
After a further two loan spells away from Benfica, Fernandes now finds himself playing in Turkey with Besiktas.
3 Steven Bergwijn January 2020
Spurs splashed out in January 2020 for Steven Bergwijn in a deal which is believed to have cost the north London club around £30m after they brought him in from PSV Eindhoven.
This seemed like a real statement of intent from Spurs given they had broken the club record transfer fee earlier in the season by signing Tanguy Ndombele.
And much like the French midfielder, it seemed as if Spurs had struck gold after the Dutchman's debut. As was the case with Ndombele, Bergwijn found the back of the net on his debut for the club in the Premier League.
However, it was only downhill from then on for the winger as he only went on to score a further seven goals in all competitions across 83 appearances for the Lilywhites (via Transfermarkt).
Just over two years later, Bergwijn left Spurs and returned to his homeland; fortunately for Spurs, they were able to reclaim most of the transfer fee for the Dutchman.
However, after his departure from N17, Bergwijn did aim a slight dig at the club with some of his comments after he left Tottenham: "It's lovely to be here with a squad that goes out to play football and that plays to win trophies," he said.
Bergwijn is yet to win any silverware with Ajax.
2 Hossam Ghaly January 2006
The name of Hossam Ghaly will forever be remembered by Spurs fans who are old enough to remember his dramatic reaction in 2007 after being taken off by manager Martin Jol against Blackburn Rovers.
Having only been brought on after 29 minutes, the Egyptian was then removed just over half an hour later for Robbie Keane, which saw the midfielder unleash his frustration.
Indeed, Ghaly removed his shirt, threw it to the ground and stormed straight down through the tunnel into the changing rooms. It is also reported that Ghaly left the dressing room before full-time to avoid the Spurs manager.
After signing from Feyenoord in 2006, Ghaly played 34 times for Spurs across all competitions, however, that game against Blackburn proved to be his final appearance for Spurs in the Premier League.
1 Ricardo Rocha January 2007
It cost Tottenham around £3m to bring Ricardo Rocha to north London from Benfica in January 2007 and that may be considered by some as £3m too much.
Rocha was brought in by Spurs to combat injury woes at the back, and he did become a regular in the remaining games of the 2006/07 Premier League campaign following his arrival.
Indeed, he racked up nine league appearances that term, however, he quickly fell out of favour in the following campaign, with his final appearance coming in September against Bolton Wanderers (via Transfermarkt).
Having then not featured for Spurs in almost two full seasons, the Lilywhites were forced to cut their losses on the Portuguese defender as he departed the club for Standard Liege in Belgium on a free transfer.
