“Tottenham are a big contender,” the Chelsea manager told the BBC. “They have bought players with quality.”
This was back in the heady days of early autumn when Tottenham harboured serious hopes of winning their first title for more than half of century as they sat second in the table ahead of Liverpool, Manchester City and Chelsea.
Tottenham might have lost Gareth Bale in the summer, but they had immediately ploughed the £86 million they received for him back in to the squad with the purchase of seven players.
In came the craft and guile of Christian Eriksen, the goals of Roberto Soldado, the drive and athleticism of Paulinho and the immense potential of Erik Lamela.
The squad was further bolstered by the arrivals of Nacer Chadli, Etienne Capoue and Vlad Chiriches.
Tottenham had swapped Bale for seven players, and it looked to have finally transformed them in to title challengers.
Seven months later, however, Tottenham are currently mired in sixth position a distant 14 points behind the leaders, Liverpool.
The title challenge never materialised, and they will also remain shut out of the promised land of the top four for yet another year.
This has been a season of spectacular underachievement for Spurs.
The Tottenham goalkeeper, Hugo Lloris, as reported in the Daily Mail, has reflected on their campaign with brutal honesty.
“It will be difficult to do worse, especially against the top four or five teams…This season we had sometimes the feeling that we give up. We can’t allow this kind of behaviour. We conceded a lot of bad defeats.”
The first casualty of these bad defeats was their manager, Andre Villas-Boas, who was sacked in December after losing 5-0 at White Hart Lane to a rampant Liverpool only weeks after being humiliated 6-0 by Manchester City at the Etihad Stadium.
But despite this slump the sacking felt oddly rash and premature.
A coach of obvious potential, Villas-Boas had finished just a point from the Champions League places in his first season at White Hart Lane, and despite the major upheaval in his playing squad, it was still seventh and only eight points behind leaders Arsenal with less than half of the season played.
There was a sense some patience with the Portuguese coach would eventually be rewarded.
Instead they swapped Villas-Boas for Tim Sherwood, who has his merits and could develop in to a fine coach, but was he really the best Tottenham could have appointed?
Did Sherwood represent an upgrade on Villas-Boas?
The decision smacked of short-termism, installing Sherwood until a better candidate became available in the summer, which effectively cast the club adrift with the majority of the season still to play.
Sherwood has revealed he wasn’t asked by the club to secure a position in the top four, a strangely pessimistic and unambitious brief.
After investing £110 million on players in the summer and removing the man who helped recruit them it seems incredible Tottenham would inform his successor his aim was to finish no higher than last season.
Meanwhile, Liverpool invested a lot less, around £40 million in the summer, and stirred by some genuine ambition have leapfrogged Tottenham from seventh to the top of the Premier League.
Sherwood has shown potential in the role, but since December has only lifted Tottenham up a solitary position from seventh to sixth.
Sherwood, however, is more bullish about his impact at the club.
"The record's good, it is better than any Premier League manager in the history of this club," Sherwood said in The Guardian. "There has been no one at this club who has done a better job at the Premier League. My record stands for itself."
A win rate of 61 percent from 18 games is better than his predecessors, but Sherwood has also overseen exits from three Cup competitions and large defeats to Manchester City, Chelsea and Liverpool.
It is increasingly clear Tottenham made a mistake back in the summer’s transfer window signing all their players from abroad, which inevitably disrupted the squad.
This batch of new players brought hope and excitement, but they also brought naivety and a lack of Premier League experience.
It would have been wiser for Tottenham to sprinkle in a few more signings from within the Premier League, whether British or foreign.
If Sherwood's win rate is not enough to save him, a new Tottenham manager will still inherit a strong foundation of players, including Hugo Lloris, Kyle Walker, Jan Vertonghen and Emmanuel Adebayor, and all of last year's signings are bound to be better and stronger players next season.
Some Tottenham fans argue this season hasn’t been an underachievement but simply what they have come to expect from their club: false hope followed by disappointment and a finish just outside the top four.
But a finish in the Champions League places was the least they should have achieved this season, and as Liverpool manager Brendan Rodgers told ESPN: “Look at Tottenham, if you spend more than £100 million, you expect to be challenging for the league.”