‘Sugar’ Ray Leonard has once again crapped out in Atlantic City.

In the first significant upset of the eWBSS (World Boxing Super Series) Middleweight Legends tournament, Ronald ‘Winky’ Wright rallied from a knockdown and a scorecard deficit to stop Leonard in nine rounds Wednesday afternoon at the Boardwalk Hall in Atlantic City, New Jersey.

Both fighters hit the canvas, with Wright down in round eight but flooring Leonard three times over the course of their quarterfinal contest, the last of which closed the show in round nine.

Leonard accomplished just about everything he set out to do over the course of a career spanning three decades. Winning a fight in Atlantic City, surprisingly, was one of the few unchecked boxes. His lone appearance in town came in 1997, when he foolishly came out of retirement to challenge Hector ‘Macho’ Camacho who stopped him in five rounds.

Sadly, that goal remains unachieved following Wednesday’s bout which featured an immensely high skill level. Leonard was sharp with his left hook, managing to time Wright’s slick defense and score upstairs. Wright—a former World junior middleweight king—pumped his jab and sought to follow with left hands but was ultimately catching more than he was able to give back.

A cut under Wright’s eye worsened by the end of round three, with his corner urging him to turn things around. The St. Petersburg, Florida-based southpaw initiated the action in round four, landing his best punch of the fight to that point when a left hand snapped back the head of Leonard. From there came two-way action, amidst what was undoubtedly Wright’s first strong round.

The next one would be even better.

Leonard took the lead in round five, the same round he failed to make it out of versus Camacho 23 years ago. The Palmer Park, Maryland legend connected with a left hook which prompted Wright to clinch. The sequence provided the weight-jumping superstar a false sense of security, as Wright found his opening late in the frame—a left uppercut which snapped back Leonard’s head.

A series of left hands would put Leonard on the canvas for the bout’s first knockdown, providing a major momentum shift for Wright.

Leonard recovered well, standing his ground in round six and defying Wright to trade with him. Both fighters had their moments in a furiously-paced round, with more two-way exchanges ensuing in round seven. Wright took the lead midway through the round, slipping a left hook to score with a three-punch combination. Leonard slipped a left late in the round to catch Wright with a left hook and straight right.

It would pale in comparison to the right hand that Leonard would land midway through round eight. Wright’s granite chin was put to the test and stunningly cracked, as he was sent to the canvas. Leonard poured on the attack once Wright made to his feet and action resumed.

Wright returned the favor at the start of round nine. A straight right hand put Leonard flat on his back, making it to his feet at the count of nine. He was sent right back to the deck, as another left put him down and this time out for the night.

The power surge was right on time, as Wright trailed 76-74 on all three scorecards. The ending was a reminder of his strong history with those dubbed ‘Sugar’, as his Hall of Fame career includes a pair of wins over former three-division champion ‘Sugar’ Shane Mosley and now a simulated victory over one of the best in boxing history.

Wright will now go on to the tournament semifinals on Saturday. Awaiting him will be the winner of the last remaining quarterfinal bout, as Hall of Famers Carlos Monzon and Jake LaMotta collide on Thursday.

The winner of Saturday’s semifinal bout will advance to Sunday’s finale.

Wednesday’s simulated bout streamed live on WBSS’s social media channel, which will carry the entire middleweight tournament.

Jake Donovan is a senior writer for BoxingScene.com. Twitter: @JakeNDaBox