Andre Villas-Boas returns to Stamford Bridge on Wednesday for the first time since the current Tottenham boss was sacked by Chelsea in March 2012.
Tottenham Hotspur's last win over Chelsea at Stamford Bridge came February 10, 1990, with goals from David Howells and Gary Lineker sealing a 2-1 win. Over 23 years on, Spurs' hopes of breaking that unfortunate run have coalesced with arguably their biggest league meeting with the Blues in that time period.
Wednesday's Premier League clash also sees Tottenham manager Andre Villas-Boas return to his old club for the first time since being sacked in March 2012. Such are the stakes at hand, the Portuguese will almost certainly put aside any personal feelings in attempting to guide his team to what be a vital three points in the competition for a top-four finish.
Over the following few pages, Bleacher Report puts forward the lineup that Spurs might, and perhaps should go with as they seek to get one over Chelsea.
Goalkeeper: Hugo Lloris
Defense: Kyle Walker, Michael Dawson, Jan Vertonghen, Benoit Assou-Ekotto.
Villas-Boas has not stuck with the same defense for two games in a row since February's consecutive Europa League meetings versus Olympique Lyonnais.
Coming up against a Chelsea side who have scored 13 goals in six games since their last loss, Tottenham cannot afford to be anything less than solid at the back. A little consistency would do no harm here.
As it happens, the above defense (who played against Southampton last Saturday) would probably be regarded as their strongest. They played in the 2-1 win over Arsenal, in what was probably Spurs' best defensive display of the last few months.
Dawson and Vertonghen will work hard to combat either Demba Ba or Fernando Torres, as well as the likes of Frank Lampard attacking from deep. Providing natural balance on both flanks, Walker and Assou-Ekotto can pitch in here too, as well as combat Chelsea's own wide threats.
Things have not always gone as smoothly as that for Spurs, and Chelsea's in-form attack will push them to the very edge. The levels of concentration and desire they displayed against the Gunners will be vital if they are to keep the Blues out—or at least stifle them sufficiently.
Midfield: Tom Huddlestone, Lewis Holtby, Tom Carroll.
Scott Parker and Mousa Dembele are doubts for Wednesday. Should neither be fit in time, it robs Tottenham of two of their more aggressive defensive midfield presences.
Without either (and long-term absentee Sandro), Spurs' best bet will be to play to the strengths of their other midfielders.
Holtby can get in and amongst his Chelsea counterparts, with his tenacity potentially a useful tool in potentially unsettling their flow. Carroll showed his willingness to pitch in too with his spirited display against Basel in the Europa League second leg.
Huddlestone's defensive aptitude of a couple of years ago (when he formed a strong partnership in midfield with Luka Modric during the climax to the 2009-10 season) has diminished somewhat. But if the above two can do the main leg work, he is capable enough to sweep up and obstruct where he can.
Going forward will be where this midfield trio can really affect the game, and possibly impose themselves on Juan Mata and co—rather than the other way around (at least not for large periods).
All three are good passers who use the ball intelligently.
Holtby has the drive that can bring Spurs forward, while Carroll's mobility gives them an outlet and link-up man between midfield and attack. It will be a big challenge for the comparatively inexperienced 20-year-old, but if he can get into the game enough, he might prove crucial in Spurs avoiding being pegged back through a lack of passing options.
Getting just an adequate balance in performing their two main duties individually, let alone between themselves, will not be easy. In the absence of players who can really stop Chelsea, for this Spurs midfield their best form of defense really is attack.
Attack: Clint Dempsey, Jermain Defoe, Gareth Bale
Aaron Lennon is also a doubt for Wednesday's game. Even if he is fit enough to feature, there is an argument that Spurs would benefit having him as an option off the substitutes' bench.
We do not know if Villas-Boas intends for his team to really take the game to Chelsea, or approach his former club more cautiously. Given the midfield possibly being without both Parker and Dembele, having Clint Dempsey in the side gives Spurs room to maneuver.
Dempsey is able to drop back and help his midfield if they find themselves under siege for a sustained periods of play. The American also offers a genuine goal threat, something he has proven throughout this season in big games versus Manchester United, Basel and Manchester City.
Emmanuel Adebayor performed decently after coming on against Southampton. But Jermain Defoe deserves to stay ahead of him up front for a few reasons.
Defoe, to be frank, works a lot harder. Spurs will need him to put the running in that might catch a David Luiz or Branislav Ivanovic off guard as they seek to apply pressure to Chelsea. Obviously there is the striker's goal threat too.
He also gives Villas-Boas some flexibility in how he might use Gareth Bale.
The Welshman's recent goals have come from him operating from right wing, but he has not always been able to involve himself as much as he might like there.
Should Villas-Boas want to deploy Bale centrally while still maintaining a primary front three, Defoe can be moved out wide and asked to cut in from there.
As has been the case this season in some of Tottenham's best wins (the move to 4-3-3 during the 3-1 over Man City being a big example), adaptability on Villas-Boas' part could be key. Spurs will hope there is plenty of back and forth in this game, as that would mean they are giving Chelsea something to think about.
If they are to get the win (heck, even just avoid losing) they will have to overcome a team full of confidence—not to mention historical disadvantage. Its not going to be easy, but if Spurs want more meaningful occasions such as this, they are going to have to get used to such challenges.