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#3 Dele Alli (MK Dons to Tottenham, 2015)
Okay, so technically speaking, Dele Alli wasn’t actually a ‘January’ signing for Tottenham. The attacker actually joined Spurs from MK Dons on February 2nd, 2015, for a fee of £5m. But as that day marked the end of 2015’s January window, it’s fair to have him appear on this list.
Alli didn’t make his first Tottenham appearance until the 2015-16 campaign, as his transfer saw him immediately loaned back to MK Dons for the remainder of the 2014-15 season.
In the time that has followed, though, he’s gone from being an unknown teenager to one of the highest-rated attackers on the planet.
Alli’s first season with Tottenham saw him waste no time in breaking into the first team, despite being just 19 years old at the time. It took him just three games to score his first goal for the club, and by November 2015, he’d impressed so much that he was called up into the England senior squad.
The youngster ended his first season at Tottenham with 10 goals – including a spectacular strike against Crystal Palace. But it was his second campaign that really marked him out as a potentially world-class performer.
The 2016-17 season saw Tottenham finish second in the Premier League – their highest-ever finish. And Alli scored a total of 22 goals in 50 appearances, a phenomenal return for an attacking midfielder.
And in the 2017-18 season, his reputation was enhanced with tremendous performances in European games against Real Madrid.
In the three seasons that have followed, Alli’s career has waned somewhat. Injuries have curtailed his progress, and he now seems to be out of favor with Tottenham boss Jose Mourinho.
However, it’s clear that he’s a phenomenal talent – and even if he never gets back to form, his early years at Tottenham definitely make him one of their best winter signings.
#4 Michael Dawson (Nottingham Forest to Tottenham, 2005)
Largely forgotten today, thanks to Tottenham’s increased reputation in the Premier League, Michael Dawson was undoubtedly one of the Premier League’s very best defenders in his prime.
Eventually acting as Tottenham’s captain, the England international was a rock in the Spurs backline for a total of 10 seasons. Dawson saw them rise from mid-table also-rans all the way to their first-ever Champions League campaign in 2010-11.
Signed from Nottingham Forest alongside teammate Andy Reid for a combined fee of £8m in January 2005, Dawson made just five appearances in his first half-season. But by 2005-06, the center-back muscled his way into the starting XI and formed a strong partnership with club stalwart Ledley King.
The duo helped Tottenham to finish in fifth place – their highest Premier League finish at the time – and Dawson received rave reviews for his performances.
Dawson remained a constant in Tottenham’s first team for the following five seasons. In 2009-10, he was a key member of the Spurs side that finished fourth in the Premier League – making it into the Champions League in the process.
And in that European campaign, Dawson was one of Tottenham’s best performers, helping to keep the attackers of Inter Milan, AC Milan, and Werder Bremen quiet in historic victories.
Injuries curtailed his season in 2011-12, but Dawson then made his way back into the first time in 2012-13 and 2013-14. He only departed the club when he was 29 years old and largely past his prime.
For his longevity and his quality, the central defender should definitely be considered one of Tottenham’s greatest January signings.
#5 Wilson Palacios (Wigan Athletic to Tottenham, 2009)
Harry Redknapp – who took over at Tottenham in October 2008 – will be forever linked with some of the wildest transfer windows in the club’s history. It was Redknapp who oversaw the last-minute signings of players like Rafael van der Vaart and Emmanuel Adebayor, but one of his best signings came in January 2009.
That window saw him bring in tough-tackling midfielder Wilson Palacios from Wigan Athletic for a fee of around £12m.
The native of Honduras was already well-known for his combative and aggressive style in the middle of the park, and he made an immediate impact on Tottenham’s fortunes. Prior to his arrival, Spurs had won just one of their previous seven games.
After Palacios arrived and added some much-needed steel to their midfield, Tottenham lost just one of their next seven – his debut game against Bolton Wanderers.
Palacios’ good form continued into the 2009-10 season, where he made 33 appearances for Tottenham in the Premier League and helped them to qualify for the Champions League for the first time.
And in that European campaign of 2010-11, the Honduran more than held his own against the midfields of teams like AC Milan and Inter Milan.
Palacios departed North London at the end of that season for Stoke City. But due to his effectiveness, should definitely be considered one of Tottenham’s best January signings.
