Tottenham Hotspur v Chelsea

Spurs had barely unpacked their Football League membership when Chelsea beat them 2.1 at Stamford Bridge in December 1909.

On 18 December 1909, Chelsea hosted Tottenham Hotspur in a First Division fixture at Stamford Bridge. Chelsea won 2–1 in what was the first competitive meeting between the two clubs. Spurs had only been elected to the Football League the previous year, and the fixture quickly became a regular feature of the London football scene.

A capital final, settled before 100,000 pairs of eyes; Spurs made sure London's first Wembley showdown was entirely their own.

On 20 May 1967, Tottenham and Chelsea contested the FA Cup Final at Wembley, the first time two London clubs had met in the showpiece match. A crowd of 100,000 watched Spurs win 2–1, with Jimmy Robertson and Frank Saul scoring for Tottenham and Bobby Tambling replying for Chelsea. It was a landmark moment for London football and cemented the fixture as something more than a routine league encounter.

Spurs beat Chelsea 3-0 in the sixth round on the way to lifting the FA Cup at Wembley; Terry Venables' side played with rare swagger that spring.

The 1990–91 FA Cup run was one of Tottenham's most storied. In the sixth round, Spurs beat Chelsea 3–0 at White Hart Lane on their way to lifting the trophy at Wembley. That season's cup run, under Terry Venables, culminated in a dramatic semi-final win over Arsenal and a final victory against Nottingham Forest. The Chelsea result was a statement of intent from a Spurs side playing with real swagger.

Ninety-five points in a single season; Mourinho's Chelsea had stopped being rivals and started being royalty.

Roman Abramovich's takeover of Chelsea in 2003 transformed the club into serial title contenders almost overnight. By 2004–05, José Mourinho's Chelsea won the Premier League with 95 points, and the fixture took on a new dimension. Spurs were no longer facing a fellow mid-table London club; Chelsea had become one of the richest and most powerful teams in European football. The rivalry gained an edge of aspiration versus establishment that persists to this day.

Woodgate, of all people, won it with his head; Spurs' first silverware in nine years, snatched from the big spenders.

The 2008 League Cup Final at Wembley saw Tottenham beat Chelsea 2–1 after extra time. Didier Drogba gave Chelsea the lead, but Dimitar Berbatov equalised from the penalty spot. Jonathan Woodgate, named Man of the Match, headed the winner in extra time to deliver Spurs their first major trophy since 1999. It was a rare moment of Tottenham supremacy in a period dominated by Chelsea's spending power.

Terry lifted the trophy, Costa did the damage, and Pochettino's promising side left Wembley empty-handed.

On 1 March 2015, Chelsea and Tottenham met again in the League Cup Final at Wembley. John Terry and Diego Costa scored as Chelsea won 2–0, with Terry named Man of the Match. For Mauricio Pochettino's young Spurs side, it was a painful afternoon, but the performance hinted at the team that would challenge for the Premier League title the following season.

Nine yellow cards for Spurs alone, yet the referee pocketed his red to protect Leicester's moment.

On 2 May 2016, Tottenham travelled to Stamford Bridge needing a win to keep their Premier League title hopes alive. What followed was one of the most ill-tempered matches in Premier League history. Spurs led twice through Harry Kane and Son Heung-min, but Chelsea fought back each time through Gary Cahill and Eden Hazard. The match finished 2–2, and Leicester City were confirmed as champions. The match saw nine yellow cards for Spurs and twelve in total. Mark Clattenburg later revealed he deliberately avoided sending off Tottenham players to prevent the narrative becoming about referee decisions rather than Leicester's achievement. The fixture earned the name 'Battle of the Bridge' and remains one of the most talked-about Premier League matches of the decade.

A single stand holding 17,500 supporters; the South Stand alone outsizes many entire grounds.

Tottenham's new 62,850-capacity stadium opened in April 2019, replacing the old White Hart Lane. The ground is widely regarded as one of the finest in world football, with its single-tier South Stand holding 17,500 supporters. Chelsea's visits to N17 now take place in a venue that matches the intensity of the fixture itself. The first league meeting between the sides at the new ground came in the 2019–20 season.

Chelsea won the latest chapter 1-0 at the Tottenham Hotspur Stadium; over a century in, the fixture still draws the Premier League spotlight.

The fixture continues to deliver. In November 2025, Chelsea won 1–0 at the Tottenham Hotspur Stadium, the latest chapter in a rivalry that has now spanned well over a century. With both clubs investing heavily in new squads and competing for European places, the meetings between Spurs and Chelsea remain among the most anticipated dates on the Premier League calendar. The return fixture at Stamford Bridge is scheduled for May 2026.