The north Londoners seriously challenged for the Premier League title for the first time in decades, in the process earning their much-desired return to the Champions League. Revitalised by the management of recent hiring Slaven Bilic and the contributions of new playmaker Dimitri Payet, their East End rivals were in contention for a while too. Ultimately qualifying for the Europa League instead, their final season at Upton Park was marked by some memorable moments.
Both will and should remember the campaign fondly. The disappointment felt at its conclusion, though—especially by Tottenham—was commensurate with the underachieving nature of this rivalry.
This has been brought to mind by the two sides' latest meeting and how their current positions contrast.
Tottenham have started the season decently, keeping in touch with the top of the table despite failing to convert draws into wins since early October. The recent form of Arsenal, Chelsea and Liverpool has, however, called into question if Mauricio Pochettino's side can get back to the heights of last season's unexpected championship chase.
Heading into the Saturday evening game, West Ham were still sitting just outside the relegation zone—a consequence of an inconsistent start to their campaign as they settled into their new London Stadium home.
Could their fortunes be about to diverge again, reminiscent of much of the last decade? Or is it something akin to the shared (relative) mediocrity of much of the 1990s that lies ahead?
They will hope it is neither and they both end up back competing in the Premier League's upper echelon. But amid all the capital enmity between these two (coming more acutely from West Ham's direction, similar to Spurs' inferiority-tinged hatred of Arsenal), it is hard to get away from this being the division's most distinct disappointment derby.
The two have enjoyed considerable past successes that have shaped respective inclinations towards upholding tradition and certain playing ideals.
In the 1960s Tottenham were led by Bill Nicholson as Ron Greenwood managed West Ham. Each won trophies at home and abroad while coaching some of the defining players of the era, the likes of Danny Blanchflower, Jimmy Greaves, Geoff Hurst, Dave Mackay, Bobby Moore and Martin Peters.
With names so evocative of a golden era in British football it is no wonder why the clubs and their fans have been enthralled by notions of playing with with style and class ever since.
Honours lists of the 1970s and 1980s continued to be peppered by the achievements of two of London's proudest. Except now the men in charge were changing to Keith Burkinshaw and John Lyall, while their squads featured Billy Bonds and Steve Perryman, Trevor Brooking and Glenn Hoddle.
Of course, there were disappointments (including relegations) and deviations away from expected standards of style and quality in-between times. But in winning and challenging for trophies in England and in Europe, Spurs and the Hammers were generally among the country's more prominent clubs.
Alas, aspiring to play the Tottenham and West Ham ways has rarely since come off with any consistency.
The difficult start they are experiencing in a potentially even more competitive Premier League season is bringing to mind the battle to ensure their continued relevancy that has defined their contributions across the turn of the century. It is one that has exacerbated these derbies' status as one of the country's most tension-filled, occasionally vicious frequent clashes.
For much of the Premier League era the teams have traded results of great worth to each other but little significance to others.
There were some exceptions in terms of the grander scheme of things—West Ham's final-day defeat of an illness-stricken Spurs meant they were pipped by neighbours Arsenal to fourth spot in 2005-06, a season later the north Londoners' comeback 4-3 victory seriously damaged the Irons' survival hopes (though they did stay up). Mostly, they have fought for immediate local bragging rights and perhaps influencing who would finish higher in mid-table.
Hammers boss Bilic this week recalled one such instance from his playing days for the club.
He made his debut at White Hart Lane in February 1996 as the Hammers won 1-0 thanks to a goal from Portuguese forward Dani. Spurs would finish the season eighth to their 10th.
"It was my first game for West Ham and it was a great night," the Croatian recalled, speaking to his club's official website. "They had a really good team but we scored early on from a corner and it was a great debut. It gave everyone a big boost at the club.
"It was a special night and I knew before the game how big it was going to be because I had been waiting for my work permit. When you play against Tottenham it is something special and I hope we can get a similar kind of result on Saturday!"
Bilic retained some perspective over the more urgent need for three points.
"We have improved a lot in recent weeks, but we are still not in a position that we want to be in," he added. "That is why we want a good result against Tottenham on Saturday and get something from the game."
In general, his enthusiasm for the occasion reflects the fact these games mean a little more to West Ham. Spurs' biggest derby is Arsenal, and games with Chelsea—by coincidence the two opponents sandwiching this fixture—also get the juices flowing (the repercussions of their volatile scrap in May still loom over them).
Though later describing it to the club's official Twitter (see above) as "a special game," during his pre-match press conference Pochettino was more interested in stressing Spurs' need to treat every game as big.
"I think that every game after two years and a half here, every time that we play and compete in the Premier League the opponent take to the game like a derby or like a final—that is good," he said.
"It is another derby or another final for us, and we felt that last season and still feel that every time we play and compete in the Premier League, the opponent they try to give their best."
Yet, when it comes to it, these games nearly always bring out heightened satisfaction or disappointment in Spurs.
Not winning the last match at the Boleyn Ground in March hurt their title aspirations but also cost their fans permanent taunting ammunition. Similar is at stake again with this being the final bout at the current White Hart Lane.
Conversely, Spurs' 4-1 win over West Ham last November (highlights below) was among their best performances. The players and supporters' reactions to the goals showed how much it meant to silence their foes.
This one is as big as any in recent years if either are to move beyond parochial concerns once more.
Both could do with a derby victory to energise their seasons. Three points alone will not get them back to where they were in the spring, but it could be a start as they head into the busiest and potentially most bountiful period of the season.
Whatever happens, the result will undoubtedly mean plenty to both and the game itself should be an entertaining one for neutrals.
But on a weekend boasting Bundesliga's Der Klassiker, the Madrid and Milan derbies, Fenerbahce against Galatasaray and an Arsene Wenger-Jose Mourinho match-up that may reignite the dormant Arsenal-Manchester United rivalry, plenty of work needs to be done for Tottenham versus West Ham to get anywhere near achieving such relevance in the footballing public's eye.
Quotes obtained firsthand unless otherwise noted.