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Anthony Joshua vs. Andy Ruiz Jr. was a heavyweight professional boxing match contested between undefeated and unified WBA (Super), IBF, WBO, and IBO champion Anthony Joshua, and former world title challenger Andy Ruiz Jr. The bout took place on June 1, 2019, at Madison Square Garden in New York City, New York. Joshua was originally scheduled to face undefeated WBA No. 2 and WBO No. 3 ranked heavyweight Jarrell Miller, who was replaced by Ruiz Jr. after Miller failed three drug tests.

After coming in as a 25–1 underdog, in a shocking upset, Ruiz Jr. won the match via technical knockout in the seventh round,[2][3] ending Joshua's undefeated record and becoming the new unified heavyweight champion. The fight is considered one of the biggest upsets in boxing history, drawing comparisons to Mike Tyson vs. Buster Douglas in 1990 and Lennox Lewis vs. Hasim Rahman in 2001.

Rounds one and two of the fight were relatively slow, with both Ruiz and Joshua feeling each other out. Through the first two rounds, Joshua had only landed nine punches out of forty seven thrown, and Ruiz only three out of thirty one thrown. Round three, however, would mark a drastic turning point in the fight.

With two minutes and seventeen seconds remaining in round three, Joshua knocked down Ruiz. Ruiz rose to his feet, seemingly unfazed by Joshua's power, and quickly resumed attacking. Mere moments after having hit the canvas himself, Ruiz responded with a succession of heavy punches; despite hitting Ruiz with repeated jabs to the face, Joshua was caught off guard by a blow to the temple which visibly staggered him, after which Ruiz quickly forced him off his feet. Joshua was able to get back up, but did not respond as aggressively as Ruiz had, instead choosing to remain on the defensive following the surprise of being knocked down. Just before the close of round three, Ruiz again managed to fell a clearly disoriented Joshua after forcing him into a corner and unleashing a series of power punches. As he got up, Joshua took the mandatory eight count before raising his gloves, indicating to the referee that he was physically able to continue. Round three ended with both fighters advancing toward one another momentarily before they were interrupted by the bell signalling the end of the round.

Rounds four, five, and six consisted of minor exchanges between Ruiz and Joshua, with both fighters seeking a mid-round rally to boost their points on the scorecards. With two minutes and twenty seven seconds remaining in round seven, Ruiz knocked over Joshua once again with a short sequence of heavy blows. In spite of this, Joshua managed to get back on his feet once again, and was able to engage Ruiz briefly before being floored for a fourth and final time, with one minute and fifty nine seconds left in the round. Almost immediately after dropping to the canvas, Joshua spat out his mouthpiece before rising, turned away from the referee, and walked somewhat unsteadily back to his corner. Joshua then faced the referee, arms resting on the ropes, and began talking to him. Seemingly disoriented and hesitant to continue the match, Joshua's responses to questioning were deemed insufficient, resulting in the referee waving off the fight. The referee subsequently awarded Ruiz a round seven TKO victory, making him the first Mexican-American and second Hispanic heavyweight champion in boxing history.

At the time the bout was stopped, Ruiz was ahead on two of the judges scorecards by 57–56, while the third had Joshua winning by 57–56.

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