Harry Kane, the Tottenham striker, said Chelsea celebrated like it had won the title. In fact, the 2-2 draw at Stamford Bridge in April meant Leicester City was champion and Spurs’ hopes of a first English crown since John F. Kennedy was inaugurated as president of the United States had disappeared after a bitter game that saw it squander a two-goal lead and collect a Premier League record 11 yellow cards.

A very bad night at the office. In fact, for Tottenham it could hardly have been worse.

After a season of post-Mourinho underachievement Chelsea, which was the reigning champion, belatedly played like a real winner when Spurs’ hopes of finishing first were on the line. For Chelsea, stopping Tottenham’s charge towards the summit of English football was a highly acceptable second to retaining the title. While Arsenal is Spurs’ natural and nearest rival, Chelsea is the real enemy, the bitterness spilling over to anti-Semitism involving Tottenham’s traditional large Jewish support.

Spurs, without a win at Stamford Bridge in any competition since Gary Lineker sealed a 2-1 victory there in February of 1990, visit Chelsea Saturday licking their wounds following the Champions League knockout after the 2-1 loss at Monaco. To put Spurs’ continued failure in West London into context, their last win at the Bridge pre-dates the inception of the Premier League and Kane wasn’t even born. It is a 29-game winless streak.

The rivalry started in the Sixties when Spurs bought Jimmy Greaves and Terry Venables, two of Chelsea’s favorite and most valuable players. This did not go down well at the Bridge. In 1967, Greaves and Venables played in the F.A. Cup final against Chelsea, which Spurs won 2-1.

Losing was bad enough, but defeat by Spurs with two former Chelsea heroes in the team was a dagger to the Blues’ heart. A new enemy was born.

For all the perceived glamour attached to Tottenham, it is, to use a Mourinhoism, a specialist in failure. The youngest fans to have witnessed the club win a major trophy — the English League (1961), F.A. Cup (1991) or a European Cup (UEFA Cup 1984 ) — will have to be at least almost 30 to have a conscious memory of any Spurs glory, yet the club still acts as if it is one of the heavyweights of English football.

Before Roman Abramovich bought Chelsea 13 years ago, those brokering a deal for the billionaire to own a Premier League club approached Tottenham. Word is Spurs did not take the request for talks seriously so the Russian’s advisers moved on to Chelsea. It was a Sliding Doors moment. The rest is history.

A particularly bittersweet occasion came in 2012. Chelsea had finished sixth and would miss out on qualifying for the Champions League unless it beat Bayern Munich in the final. The bonus for Chelsea was that its success against the Germans meant Tottenham missed out on Europe’s premier club competition the following season. A double triumph.

Today the title is not up for grabs and on the face of it, there should be little pressure on manager Mauricio Pochettino as Spurs prepares for the match. While Chelsea is top of the Premier League, Tottenham is sixth, just four points behind the Blues. Spurs are the only unbeaten team in the league and have the best defensive record.

However, their underachievement in the Champions League has angered Spurs fans — three defeats and four points from five games in what seemed one of the less demanding groups highlighted the lack of strength in depth at Pochettino’s disposal. He said he needs to bring in more players to compete at that level, though he loses sympathy after paying £30 million for Newcastle’s Moussa Sissoko, who has started only four league games and £17 million for Vincent Janssen of AZ Alkmaar last summer.

Pochettino decided to leave out Kyle Walker and Jan Vertongen, half of Spurs’ first-choice back line, against a Monaco team that is averaging three goals a match in Ligue 1 to keep them fresh for Chelsea. The first aim of the Premier League’s elite is to qualify for the Champions League. Having done this, and Pochettino is not alone, too many field weakened sides in Europe, preferring to rest key players for the subsequent league match where victory would help them reach the following season’s Champions League.

The Argentine has a significant decision to make when CSKA Moscow comes to Wembley, Spurs’ adopted European base while White Hart Lane is being enlarged, for the final group match. It is an 80,000 sellout, though how many actually turn up now that Spurs cannot advance to the knockout stage of the Champions League remains to be seen.

Spurs must avoid defeat against the Russians to qualify for a place in the Europa League and whatever he may say in public, Pochettino wants Thursday night football next spring like he wants a full-blown injury crisis.

It is unthinkable the manager will select a strong or even a strongish team, but a side of enthusiastic youngsters keen to make their mark and who would relish playing at Wembley could give Tottenham the ultimate European consolation prize. Rarely would defeat be so acceptable, even celebrated.

Spurs were second best in every department against a spirited and skilful Monaco, but on current form Chelsea, with six wins from its last six games, is playing as well as any team in Europe. Antonio Conte has switched from a back-four to a three-man defense in which David Luiz, ridiculed by most when he returned to the Bridge last summer, is outstanding. Chelsea has not conceded a goal in seven matches and the defensive system that worked so well for Conte at Juventus has hit the ground running at the Bridge.

Marco Alonso and Victor Moses are unlikely but hugely effective wing-backs and Pedro is playing so well Willian, Chelsea’s best player for most of the past year, cannot get in the team. Eden Hazard is thriving under Conte and while Diego Costa will always play close to the edge, the Spain international is not at war with everyone these days and is the Premier League’s leading goalscorer. Branislav Ivanovic, Oscar, John Terry, Cesc Fabregas and Michy Batshuayi, a £33 million signing from Olympique Marseille in July, represent a substitutes’ bench Pochettino can only dream of.

Tottenham may extend its unbeaten Premier League run, though is unlikely to end its winless streak at the Bridge.

Christopher Davies was a longtime Premier League correspondent for the London Daily Telegraph.

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