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Boxing

British boxers as big underdogs: The fighters who dared to take down Mike Tyson, Roy Jones Jr and Canelo Alvarez

Christopher Walker
British boxers as big underdogs: The fighters who dared to take down Mike Tyson, Roy Jones Jr and Canelo AlvarezGettyImages

John Ryder aims to cause a huge upset this weekend when he looks to become world champion at 168lbs by defeating Canelo Alvarez.

The fight, showing in multiple regions on DAZN, sees Ryder travel to Mexico looking to shock the local favourite. He's not the first Brit to be in such a position as DAZN looks back at the fighters who've tried cause a massive shock.

Mike Tyson vs. Frank Bruno, 1989  

Despite being the darling of his nation, Frank Bruno’s attempts to become heavyweight champion of the world had been derailed by Tim Witherspoon in 1986. Three years later, Bruno had restored his confidence and he was aiming to cause a seismic shock by ending the dominant reign of Mike Tyson. 

After making a good start in the contest that included stunning the Brooklyn fighter in the opening round, Bruno couldn’t find anything else to disrupt the champion’s momentum. Tyson found the form that made him boxing’s most feared fighter at the time as he stopped an outgunned Bruno in five rounds. 

Roy Jones Jr vs. Clinton Woods, 2002  

Clinton Woods had built himself a stellar reputation at domestic and continental level, but he quickly found out that wouldn’t be enough when taking on Roy Jones Jr. The Florida man was boxing’s most outstanding fighter for the majority of the 1990s and he carried that form into the early millennium on his way to becoming heavyweight champion in 2003. 

Against Woods, Jones Jr demonstrated his vast repertoire of skills as he outclassed the proud Yorkshireman from the outset before the fight was stopped in the sixth round. Woods would go on to become world champion three years later, but on this night, he came up against arguably the best version of Jones Jr. 

Canelo Alvarez vs. Rocky Fielding, 2018  

Liverpool’s Rocky Fielding had already caused a major upset in 2018 when he travelled to Germany in the summer to dethrone Tyrone Zeuge for WBA honours at super-middleweight. Rocky’s reward was a showdown with Canelo Alvarez at Madison Square Garden six months later. Could he flip the script for a second time? 

The answer was an emphatic no as Canelo displayed his ruthlessness to make Fielding’s reign a brief one. Landing hurtful body shots from the start, Canelo was able to drop Rocky in each round before the fight was stopped in the third stanza. Fielding went down fighting but it was a harsh lesson about how brutal boxing can be at the elite level. 

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Vitali Klitschko vs. Danny Williams, 2004  

Danny Williams’ 2004 victory over a broken Mike Tyson shouldn’t have been the pathway to a world title fight with the menacing Vitali Klitschko. Williams was a solid contender but his win over Tyson elevated him to a level that he probably had no business occupying and Klitschko proved that in a destructive manner. 

Making the first defence of his recently acquired WBC belt, Klitschko was ruthless from round one as he hurt Williams on multiple occasions. After repeatedly hitting the floor and failing to make any dent on Klitschko, Williams was rescued in the eighth round. 

Miguel Cotto vs. Michael Jennings, 2009  

No one was sure what to expect when Miguel Cotto made his return to the ring following his controversial loss to Antonio Margarito in the summer of 2008. Cotto had been battered by his Mexican rival but a major issue surrounding Margarito’s hand wraps would forever tarnish the brutal classic. 

Cotto would face Chorley’s Michael Jennings for the vacant WBO belt and it quickly became clear that the Margarito loss had no lasting impact. After dropping Jennings twice in round four, it became apparent that the end was near. Cotto continued his assault in the next round and the fight was sensibly stopped by the referee.