UFC Hall of Famer Matt Hughes will go down as one of the all-time greats to ever grace the cage.

However, that doesn’t mean Hughes has had a perfect career.

Despite going 45-9 and capturing a pair of UFC welterweight titles, there are a few matches that the former NCAA Division I wrestler would likely prefer to have back.

So, let’s take a look at five losses that helped shape the career of Matt Hughes:

1. Josh Koscheck, UFC 135 (2011)

This is likely the one that Hughes will look back at most when reflecting on why he decided to retire.

It had been several months since Hughes last fought – another knockout loss we will cover later in this article – and the former champ was looking to possibly go out on top by defeating Josh Koscheck.

Instead, it was Koscheck who controlled the action. Using his size and speed to his advantage, “Kos” dominated the stand-up. Hughes was never able to take Koscheck down and execute some vintage ground-and-pound, and eating a fight-ending combo finished his night and career.

Koscheck earned the win via knockout with one second left in the first round.

2. Georges St-Pierre, UFC 79 (2007)

Hughes had plenty of trouble with current UFC Welterweight Champion Georges St-Pierre during his career, posting a 1-2 record against the Canadian.

Of the two defeats, though, the one at UFC 79 stands out.

With just six seconds remaining in the second round, Hughes was forced to submit to an armbar.

St-Pierre put on a complete display, showing all other welterweights out there that he was the new king at 170 pounds. GSP fended off each takedown attempt, puzzling the former wrestler.

St-Pierre proceeded to place Hughes on his back in the second before locking in the fight-ending submission.

3. Thiago Alves, UFC 85 (2008)

This one was likely a fight that the UFC asked Hughes to take – and he accepted, as he always did.

Alves was an up-and-coming prospect in the division and would eventually challenge for the title. The fight took place in England, one of just a handful of bouts Hughes would ever have outside the U.S.

Maybe he was still suffering from the side effects of the loss to GSP, or maybe it was jet-lag, but Hughes never looked like his old self against Alves. The younger fighter constantly defended against Hughes’ takedown attempts.

In the second, Alves went on the attack, catching Hughes with a huge knee early, opening up a cut. Alves continued to pound away before the fight was stopped just 62 seconds into the round.

4. Dennis Hallman, UFC 29 (2000)

Much like that first career defeat, most fighters will always remember their first loss inside the Octagon.

For Hughes, both of those center around one man: Dennis Hallman.

Hallman handed Hughes his first career loss in 1998 in his fifth professional fight, while also defeating him in his UFC debut in 2000. Both Hallman wins came via submission.

While Hughes went on to bigger and better things as evident by his resume, Hallman’s biggest claim to fame is his two wins over Hughes.

5. BJ Penn, UFC 46 (2004)

Following five successful title defenses of the UFC welterweight belt, Hughes was matched up with rising star BJ Penn in 2004.

Having just submitted Frank Trigg and bested Sean Sherk the previous year, Hughes looked to add Penn’s name to his legacy.

However, in three trips to the cage with “The Prodigy,” he would only win once, as Penn scored a first round submission over him in 2004, and followed up with a knockout victory in 2010.