This weekend, the odds are stacked against them breaking that duck too, with Spurs flying in second and the Swans struggling in 16th. Both need the points though, even if they are for completely different reasons, and it so it promises to be a well fought game between two sides who like to play good football.
Spurs come into this game full of confidence, even if they did succumb to a 1-0 defeat to Crystal Palace in the FA Cup last weekend.
As they continue their Premier League title challenge though, sat second in the table and just two points behind leaders Leicester City, fatigue could start to kick in with them playing Thursday and Sunday on a regular basis.
Swansea, meanwhile, are looking to end February by bagging their first win of the month, with their last victory a 2-1 win at Everton at the end of January.
Since then, they've had to settle for draws with West Bromwich Albion and Palace, which were followed up with a disappointing defeat to Southampton last time out.
With a week off under their belts, however, the players will be well rested after a busy period and raring to go again against a tired opponent.
As aforementioned, the last time the Swans beat Spurs was back in the 1980s. They won two of the first three meetings with Tottenham, but have lost eight of their 10 encounters since.
They managed a 1-1 draw in 2011 on their return to the top flight, that being their first meeting with Spurs since a 1-0 loss in 1983, but then endured a seven game losing streak against their Premier League rivals.
That was ended back in October in a 2-2 draw at the Liberty Stadium, but they remain the underdogs today, especially since they have never taken points off of Spurs at White Hart Lane.
When they last met in North London - in March of last year - the hosts came out 3-2 winners.
Nacer Chadli broke the deadlock after just seven minutes as Spurs raced into a 3-1 lead - goals from Ryan Mason and Andros Townsend following Ki Sung-Yueng's equaliser. Gylfi Sigurdsson, a former Tottenham man himself, narrowed the deficit to just the one goal late on, but with only one minute of normal time to play, it was a lifeline that the Swans needed to come much earlier.
Sigurdsson is in line to face his former club, whilst former Spur Kyle Naughton could also make an appearance - albeit most likely off the bench, going by recent games.
With no injury concerns for Francesco Guidolin to worry about, aside from his own struggles with illness, the Italian coach could name the same line-up that faced Southampton, though he is likely to want to make changes after such a disappointing display.
Spurs will be without Mousa Dembele, on the other hand, who is expected to be missing for two weeks with a groin injury. Harry Kane missed Thursday's encounter with Fiorentina, but will be fit for this game with the aid of a mask, it is anticipated, after he broke his nose against Palace.