Oscar De La Hoya has an uphill battle come Sept. 18. For the first time in his career, he'll be an underdog, and he's expected to be at a significant size and power disadvantage when he steps in the ring with middleweight king Bernard Hopkins – the ruler of the division since 1995.

And while a “Golden Boy” victory is unlikely, it is certainly not impossible. Since 1980, the boxing world has seen its share of shockers. Here's a list of the biggest upsets of the last quarter century.

10. Kirkland Laing W 10 Roberto Duran (1982): Granted, this was not the Duran who dominated the lightweight division in the 1970s, or even the inspired “Manos de Piedra” who worked over Sugar Ray Leonard and, later, Iran Barkley. No, this was the lazy, bored Duran who would have rather been playing his bongo drums than swapping punches. Laing was brought in as an opponent to help Duran get his groove back. Instead, Laing dominated a listless legend. He started out tentative, and became bold as the fight wore on, connecting with big right hands. Laing won a unanimous decision, seemingly ruining Duran's career. But the amazing Panamanian would come back twice more, completing an extraordinary career.

9. Azumah Nelson KO 8 Jeff Fenech (1992): Eight months earlier, Australia's multi-champion Fenech had been the victim of one of the worst draws in featherweight history. He had dominated Nelson with a ferocious two-fisted attack that may have been the highlight of a glorious career. But he was shafted, and so the rematch was made for Fenech's native Australia – where 90,000 strong showed up in support of the hometown hero. Nelson, though, was the man to reassert his greatness in the WBC featherweight title fight by executing a perfect jab-and-move gameplan. It started with a left-right hand in the first round that dropped Fenech, and Nelson proceeded to destroy him in shocking fashion. It may have been the prime performance of “The Professor's” career.

8. Vince Phillips KO 9 Kostya Tszyu (1997): Going in, Tszyu was the unbeaten hotshot of boxing – a fighter expected to be the face of the junior welterweight and welterweight division for the next era. Not to mention, he had a multi-million dollar showdown with Oscar De La Hoya hanging in the balance. But Phillips, who had been knocked out by Ike Quartey the previous year, destroyed the De La Hoya possibilities – and Tszyu's aura of invincibility – with a draining assault in one of the year's best fights. The pair battled on even terms most of the way, but Phillips' superior strength and chin proved the difference. A devastating combination trapped Tszyu in a corner and left him out on his feet, prompting referee Benji Estevez to save him. In a word, it was unbelievable. Phillips never quite capitalized on the win, while Tszyu rebounded and hasn't lost since.

7. Hasim Rahman KO 5 Lennox Lewis (2001): Lewis was considered pretty much unbeatable in light of a weak heavyweight division. He had just boxed David Tua silly and destroyed both Michael Grant and Frans Botha. Naturally, though, he became lackadaisical in his dominance, and didn't take a tough-but-limited challenge like Rahman seriously. And who would blame him? “The Rock” had come off the floor to beat Corrie Sanders the previous year, and didn't appear to be capable of competing with a guy of Lewis's size and ability. But Rahman rocked Lewis with right hands continually, and set a pace that wore down the undertrained champion. Then, boom! One right hand ended Lewis's reign. He'd pay Rahman back seven months later.

6. Vernon Forrest W 12 Shane Mosley (2002): Mosley was regarded as the best fighter in the world, pound-for-pound, when he stepped in the ring with old nemesis Forrest in defense of the WBC welterweight title. The pair was familiar with one another: Forrest had beaten Mosley in the amateurs, and “Sugar Shane” vowed revenge. Most of the boxing world figured Mosley would get it with relative ease, since he was in the prime of his career and looking more invincible by the fight. But Forrest had the book on Mosley, and utilized his height and reach – dropping Mosley twice in a shocking second round. It was easy for “Viper” from there, as he pecked away at a wounded Mosley. The decision was a formality. The rematch was six months later, and Forrest repeated the decision win.

5. Evander Holyfield KO 11 Mike Tyson (1996): Going in, this WBA heavyweight championship mirrored the 1974 George Foreman-Muhammad Ali fight. Like Foreman, Tyson was thought to be a monster who could not be slayed. Yes, he had been knocked out by Buster Douglas six years earlier, but that was considered an aberration. Since that time, and after a three year prison sentence, he had regained the merciless form that dominated the division in the late 1980s. Holyfield, like Ali, was thought to be washed up and, quite possibly, a health risk. But Holyfield stood up to Tyson's bully tactics, swapped punches with him fearlessly, and wore him down with body shots. By the end, Tyson was a stumbling, incoherent ex-champion who had been bested by a superior fighter. The rematch seven months later was similar, which is why Tyson bit off a chunk of Holyfield's ear in frustration.

4. Lloyd Honeyghan KO 6 Donald Curry (1986): Most weren't even sure how to pronounce Honeyghan's name when he challenged pound-for-pound king Curry for the undisputed welterweight title. The skinny on him was that he was tough, but few figured he'd have the skills and determination to upset a fighter of “The Cobra's” skills. Afterall, Curry was a perfect fighting machine – one who threw economical, powerful, timely punches while displaying an airtight defense. But, like Holyfield against Tyson 10 years later, Honeyghan showed no fear of Curry's reputation – and took the fight to the champion. He cut Curry, hurt him with a right hand early on, and never allowed Curry to set himself or recover from punches. The fight was stopped on cuts, and Curry went from boxing’s next superstar to a major disappointment virtually overnight. Honeyghan reigned for three years. The pair never fought a rematch.

3. Michael Spinks W 15 Larry Holmes (1985): No light heavyweight champion had ever defeated a heavyweight champion going into this fight for Holmes' IBF crown. Not Billy Conn. Not Bob Foster. Not Archie Moore. So Spinks was up against a wall to be sure. Meanwhile, the 48-0 Holmes was in the midst of pursuing Rocky Marciano's undefeated record of 49-0. So King dubbed it “A September to Remember”, because, barring a draw, history would be made one way or the other. Spinks was the one who made it with a smart, jab-and-move attack that baffled the aging champion. Spinks unleashed his punches in bunches, threw Holmes' timing off with unpredictable side-to-side movement and used his fresh legs to escape the counters. It won him a decision on this night, and another decision in the rematch seven months later.

2. Sugar Ray Leonard W 12 Marvin Hagler (1987): Hagler was the Bernard Hopkins of his day. He had made multi defenses of his middleweight title, cleaned out the 160-pound division and established himself as a superstar with a vicious knockout of Thomas Hearns two years prior. He was considered the best fighter in boxing. Leonard, meanwhile, hadn't fought but once in five years – that an uninspiring, up-off-the-floor 9th-round knockout of journeyman Kevin Howard. He had also never fought at middleweight – and Sugar Ray was installed as a solid underdog. But a rejuvenated Leonard displayed the speed and quickness of his welterweight prime, and executed a flawless gameplan of movement and mind games. He stayed on his toes throughout, and when Hagler closed in, he'd flurry out. Leonard won a close, controversial split decision that cemented his status as the fighter of the 80s. Hagler never fought again.

1. Buster Douglas KO 10 Mike Tyson (1990): The granddaddy of all upsets, everyone remembers the aura that Tyson carried into the ring with him like the towel draped around his shoulders. At the time, Tyson was a terror – the T-Rex of the boxing world with no competition in sight. He had blown away 10 title challengers, and he was two years removed from one of the more ferocious knockouts in boxing history: The 91-second demolition of Michael Spinks. After a so-so defense against Frank Bruno, Tyson had reestablished himself with another quickie KO of Carl “The Truth” Williams – considered one of the last few bonafide threats remaining. The only real challenge remaining was former cruiserweight king Evander Holyfield, who Tyson signed to fight in June 1990. To stay sharp and build up the gate for the multi-million dollar Holyfield showdown, however, “Iron Mike” signed to fight journeyman James “Buster” Douglas in February 1990. It wasn't considered so much a championship fight as a glorified sparring session. Douglas had some nice skills – especially a rocket jab – but regularly displayed a serious lack of heart. So, the thinking was that when the going got tough, Buster would fold along the dotted lines.

Douglas entered the Tokyo ring a whopping 42-1 underdog, and most Las Vegas oddsmakers didn't even bother to post it. But Douglas was inspired by his mother, who had died in the weeks leading up to the fight. And when he entered the ring, it was obvious this was not the same Douglas who quit against Tony Tucker in 1987. Slim and trim, he stuck his jab in Tyson's face from the get-go, never allowing the champion to get inside to land his big bombs. He mixed in right hands and left hooks and, soon enough, a welt developed under Tyson's eye. More rounds went by, and Douglas continued to dominate – helped along by a Tyson corner that wasn't qualified to work a three-rounder between a pair of novice amateurs. By round eight, Tyson seemed to be wilting, while Douglas was gaining in strength. Then, boom! A sudden Tyson right uppercut sent Douglas to the deck. But Buster, displaying a grit he never showed before and never showed again, got up, survived the round, and continued his domination of the “Baddest Man on the Planet”. He punished Tyson in round 9, and by round 10 the champ was done. Douglas connected with the uppercut of the century, followed by a mean left-right that sent Tyson to the deck, staring at the ceiling. A dazed Tyson tried to find his feet while simultaneously pawing for his mouthpiece, and was counted out.

Douglas had done it, and HBO's Jim Lampley – as shocked as the rest of us – put the shocking proceedings in order: “Say it now, gentlemen: James “Buster” Douglas, heavyweight champion of the world.”

Matthew Aguilar may be reached at maguilarnew@yahoo.com