As Eubank and Benn prepare to meet once more, here are five more terrific nights in Tottenham

Chris Eubank Jr and Conor Benn  fought in front of a sell-out crowd at Tottenham Hotspur Stadium back in April, producing a slugfest of a fight.

An exhausted Eubank Jr ended up on top of the encounter, but Benn will be out for revenge on September 20th, when the pair renew aquaintances for the rematch.

A state-of-the-art facility that proven more than capable of hosting boxing, the Tottenham Hotspur Stadium is currently contracted to stage Eubank Jr-Benn II - but a venue has yet to have been confirmed. 

Opened in 2019, the stadium has already hosted several blockbuster nights of boxing. However, the connection between Spurs and the sweet science goes back much further.

White Hart Lane first staged a boxing match in 1922, becoming the first open-air venue in Britain to host a fight – between Jim Smith and Pat King.

Here, we look back at five of the most notable bouts held at both the old and new White Hart Lane.

Wartime warriors battle in broad daylight – 1942

Boxing has long been one of Britain’s favourite pastimes – and not even a world war could stop the sport. In 1942, Freddie Mills challenged Len Harvey for the British and Empire light-heavyweight titles, with the fight staged during the day due to wartime blackout restrictions.

There was a distinct Royal Air Force flavour: Mills and referee Eugene Henderson were sergeants, while Harvey was a pilot officer.

Remarkably, footage still exists of the contest – showing ‘Bournemouth Bombshell’ Mills sending the champion Harvey out of the ring in the second round.

Barry Hearn’s first foray into boxing – 1987

Today, the Hearn name is synonymous with British boxing – but long before Eddie Hearn helped arrange Eubank Jr v Benn, his father Barry was taking his first steps into promotion.

Barry Hearn’s first major promotion was a heavyweight clash between Frank Bruno and Joe Bugner at White Hart Lane in 1987.

Matchroom had to hand over 10 per cent of the gate receipts to stage the fight at Spurs’ stadium, but with over 35,000 in attendance and £1 million taken at the gate, it paid off. Bruno won by eighth-round stoppage, edging closer to a dream clash with Mike Tyson.  

First world title fight ends in tragedy – 1991

Four years after Bruno vs Bugner, Matchroom returned to White Hart Lane for a world title bout – but this one ended in tragedy.

Chris Eubank Sr defended his WBO super-middleweight title against Michael Watson in a rematch of their close contest earlier that summer. Watson was ahead on points going into the 11th round and knocked Eubank down – only for Eubank to rally with a brutal uppercut in the closing seconds.

Watson collapsed after the 12th and received no immediate medical attention. With no ambulance or paramedic on site, he waited 28 minutes before being taken to hospital. He spent 40 days in a coma and underwent multiple surgeries to remove a blood clot on the brain.

Though partially paralysed, Watson later learned to walk and speak again, and in recent years has completed a mile-long charity walk at the age of 60.

New stadium, new heavyweight champion – 2021

Anthony Joshua was originally expected to headline the first boxing event at the new Tottenham Hotspur Stadium in 2020, but the COVID-19 pandemic delayed those plans.

Instead, it was Oleksandr Usyk who would make history in 2021, dethroning Joshua in front of 65,000 fans with a clinical unanimous decision. Usyk claimed the IBF, WBA and WBO belts, beginning a new era at heavyweight.

Chris Eubank Jr claims victory over Conor Benn in grudge match – 2025

Ian Walton/Matchroom Boxing

The first meeting between Chris Eubank Jr and Conor Benn may not have had any world titles on the line, but it certainly produced a phenomenal main event.

First scheduled for the O2 Arena in October 2022 before a cancellation caused by a postive drugs test for Benn, the reorganised card took place on Saturday, April 26.

Originally a continuation of their rivarly shared by their fathers, Chris Eubank Sr and Nigel Benn, in the 1990s, the war of words between the pair made the beef more than personal.

Having attracted the attention of the British public, there was plenty of money on the line, but both fighters fought with the passion and desire fuelled by the pursuit of bragging rights.

After an exhilarating fight, it was Eubank Jr who took the unanimous decision, alebit at great cost. Dehydrated and exhausted, 'Next Gen' was rushed to hospital, where he made a full recovery.

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