Tottenham's season kicked off with aspirations of ending a fifty-five-year wait for a domestic league title, but for Spurs to break that unwelcome streak, the club must dip their toe into the transfer market this winter.
The season started off so brightly for Mauricio Pochettino's side as the club remained unbeaten until November, but unfortunately of the Lilywhites, a run of zero victories in eleven games saw the wheels of fall off their campaign.
Spurs crashed out of the UEFA Champions League before falling down the table, where they now find themselves ten points behind Premier League leaders Chelsea at the summit.
The North Londoners need to make some January moves, with certain players departing the club and Pochettino replacing them with adequate upgrades to strengthen the Spurs squad at his disposal.
So, we take a look at two players Pochettino must sell and two players he must buy this winter.
Tom Carroll
Tottenham handed Tom Carroll a new contract in September but we can only assume that was to protect the midfielder's value.
He's way down the pecking order in the engine room and hasn't shown much improvement since making his debut back in 2012.
No doubt, Carroll is a talented, highly-technical player. But now aged 24, it's getting to the point where he's worth more to Spurs in the transfer market than on the pitch.
IN - Wilfried Zaha
Spurs have lacked a fast-paced, width-creating winger since the days of Aaron Lennon and Gareth Bale.
The Crystal Palace star would solve the lack of pace currently in the Tottenham XI and he's been in exceptional form for Alan Pardew's side this season.
No Englishman contributed to more assists this season than Zaha, who has also averaged the second-most successful dribbles per match of any Premier League player after Middlesbrough's Adama Traore.
OUT - Kevin Wimmer
The Austrian international has regularly disappointed for the North London outfit this season - most notably when Toby Alderweireld was absent through injury.
To remain the club's third choice centre-back, he must sacrifice the progression he could potentially make elsewhere. Wimmer is not a poor defender but a move would best suit all parties.
IN - Solomon Rondon
The Venezuelan forward has proven his ability to perform well in the Premier League. At West Brom, Rondon continues to prove worthy of the record-breaking £14.5million fee the Baggies paid for him in 2015.
Rondon could provide back-up to Harry Kane as a more experienced and proven option than Vincent Janssen, who has really struggled to find the net since his summer move from the Eredivisie - still awaiting his first goal in open play.