BoxRec

Oscar DelaHoya

Pernell Whitaker

Shane Mosley

Floyd Mayweather Jr.

Manny Pacquiao

I'll assume all are at Welterweight:

Leonard TKO12 Oscar DelaHoya - competitive, but Leonard ahead the whole fight

Leonard UD15 Pernell Whitaker - clear decision, though Whitaker makes him miss a lot

Leonard UD15 Shane Mosley - wide decision.

Leonard UD15 Floyd Mayweather Jr. - Floyd lands at a higher %, but Leonard throws more, lands more and lands more powerfully all night long. Clear decision win to Leonard, something like 10-5 in rounds.

Leonard UD15 Manny Pacquiao - The closest fight and an absolute war, but Leonard takes it 143-142 and 144-141 x 2.

Honestly, I would take Leonard to beat them all.

However, I could be persuaded that Whitaker, Pacquiao & Mayweather were each superior fighters pound-for-pound. It's a debate.

He's just flat better than De La Hoya & Mosley.

He wins them all but absolutely dominates Mosely and Pacquiao.

No doubt for me Leonard beats them all.

I think Whitaker would have be his toughest opponent, but still see Ray winning a clear UD.

He would have stopped De La Hoya in around 9 rounds no doubts, and because of Pacquiao's aggressive style I can actually see him getting stopped late as well.

Mosley loses by wide UD.

Once PBF realises he's in with a fighter who is faster, stronger, hits a lot harder and is just as skillful as he is with a real desire to fight he would do his giant turtle impression, stink the joint out and probably start demanding drug tests inbetween each round!!!
Another lopsided UD for Leonard.

Leonard beats them all on points.

He'd struggle with Whitaker the most, probably Pacquiao the least.

Him vs Pacquiao and Mosley would be the most fan friendly fights. The others wouldn't be most see, in particular vs Mayweather.

Leonard wins them all.

Moseley would be the best fight to watch. Whittaker would be the hardest man to beat but at the same time Sweet Pea would never look like he could win the fight.

Pac has the best chance but the size difference would be too much.

Ditto with the above, a peak Leonard beats them all

De La Hoya would be a rough fight early on but Leonard would take over down the stretch. Probably the most physically taxing fight of the bunch. Leonard close but clear on points.

Whitaker would look like he was being attacked by a bee hive but wouldn't be able to mount much of an offense of his own due to the massive height and reach disadvantage. Leonard wide on points.

Mosley would simply be outmatched in boxing ability. He'd land some good shots but would overall get pounded around like he was against Forrest. Leonard by dominant decision or late TKO.

Mayweather would do somewhat similarly to how Whitaker did except for he'd land more but also take more in the process. Leonard wide on points.

Pacquiao gets knocked out in the late rounds after chasing Leonard around and getting his face busted into the proverbial pizza.

He beats them all by KO...Too much skill, grit and determination for all of them. The great Sugar Ray Leonard was in a different class.

Modern day Legend.

He was truly a fighting legend and he beats them all.

Too fast, too smooth and hits too hard for all of them, not to mention fantastic chin and guts.

I do think Whittaker pushes him the hardest, but still loses widely.

W UD Oscar DelaHoya

W UD Pernell Whitaker

W UD Shane Mosley

W UD Floyd Mayweather Jr.

W UD Manny Pacquiao

All these guys lose to the Fabulous 4 of Hearns, Leonard, Hagler and Duran

elmersalsa wrote:All these guys lose to the Fabulous 4 of Hearns, Leonard, Hagler and Duran

For the most past, they arent fair match-ups in terms of weight, though.

Pfffft, Leonard isn't even in my all time top 10 p4p.

Not in mine either but he still wins all these.

SaadOffTheDeck wrote:Pfffft, Leonard isn't even in my all time top 10 p4p.

He is not in my top 10 p4p, either, but to me, he gotta be in the top 15 or 20 all-time. Great fighter.

elmersalsa wrote:

SaadOffTheDeck wrote:Pfffft, Leonard isn't even in my all time top 10 p4p.

He is not in my top 10 p4p, either, but to me, he gotta be in the top 15 or 20 all-time. Great fighter.

What is your top 20?

And the merry-go-round starts again