He returns to the ring next weekend against Jessie Vargas. It is fair to say Manny Pacquiao will likely go down as one of the greatest fighters ever to have stepped between the ropes when all is said and done.

Dream Manny Pacquiao Fights

His insatiable work ethic both in and out of the ring have elevated him beyond the realm of mere sport and have cemented him as a cultural icon, the likes of which we may not see again for a very long time.

An icon and star that continues to shine bright with kindness exhibited by him too – as evidenced by this recent admission about just how much money he has donated to his home country over the years.

While he has faced the best of the best in his own time, and hopes to climb the mountain once again on Saturday November 5th against welterweight champ Jessie Vargas, I can’t help but wonder how the ‘Pacman’ would have dealt with some of the greats from alternate eras. No decade in history off-limits.

With a plethora of legends of all styles, shapes and sizes to choose from, here are my top 5 dream Manny Pacquiao match-ups:

Roman Gonzalez

Despite both being currently active, this hypothetical dream match will remain exactly that due to weight difference.

Still, the idea of a young flyweight Emmanuel Pacquiao engaging with the current #1 Pound for Pound ranked fighter in the world is a concept too juicy to ignore.

At the time when he was a flyweight Pacquiao still had much to learn before he would evolve to become the superstar that he is today.

That naivety and lack of experience, however, took nothing away from his already super-quick fists and one-punch knockout power.

Whether or not an in-his-prime ‘Chocolatito’ would have been too much too soon for the young Filipino remains a mystery. One thing is for sure, with the hindsight we have now, this would have been one for the history books.

Naseem Hamed

The ‘Prince’ of boxing was always one for putting on a show, both during and before a fight.

His exceptionally unorthodox movement may have landed him in hot water on multiple occasions, but his ability to spring forth off the back foot, shifting his weight with superb one-puch knockout power was something to behold.

I think if these two ever would have met, after some predictably standard show boating from Hamed, Pacquiao would have mixed up his angles and finished this one quick – Hamed always favoured leaving his chin hanging like a wet towel in the wind.

But imagine the hype this one would have generated, and I’m sure the ‘Prince’ would have offered more than our money’s worth in spectacle.

Sugar Ray Leonard

Most of you will have seen this one coming.

Arguably the most idolized and revered name the welterweight division has ever produced (Sorry, Floyd). Leonard’s status as one of the most exciting fighters in the sport’s history was well accepted, even after his first loss against a robust Roberto Duran.

While Leonard would have a distinct height and reach advantage over ‘Pacman’, these kind of statistics have never stopped him mixing it up with (in some cases dominating) larger opposition.

It would be an unmissable combination of styles and ring-savvy, the kind of legendary matchmaking promoters can only dream of.

Roberto Duran

The above two names can never seem to escape each other, can they?

Just looking back at the Leonard/Duran saga it’s clear to see the fights would have taken very different paths should Leonard’s name be substituted with that of Pacquiao.

While Leonard mostly favoured a back-foot approach, Duran and Pacquiao surely would have gone to war with one another in a similar fashion how Pacquiao went to war with Juan Manuel Marquez.

I imagine Pacquiao would try to keep it technical at first, but the aggressiveness of Duran would surely cause a descent into complete boxing anarchy.

Two of the hardest hitting welterweights in their prime slugging it out, it would have been magical.

Sugar Ray Robinson

The second ‘Sugar Ray’ to appear on this list, but by no means least.

While Muhammad Ali laid claim to the title of ‘Greatest of all time’, many agree this man is the rightful holder of that particular crown.

Robinson was the undeniable kingpin of boxing in the 1940’s and early fifties. During a time when the sport was a very different place and where professionals would take any fight at the drop of a hat, his unheard of speed and brick-like fists were the stuff of legend.

The skills and ring-awareness required to survive in today’s boxing world may have become more refined, especially when you look at certain cases like Pacquiao – a technical master, but that doesn’t stop me from pondering what a fight between these two in the Sugar Ray Robinson era of boxing would have looked like.

Would Pacquiao have been able to manage Ray’s overbearing size and power? He was, after all, a huge welterweight.

Or would Manny have worked his way into the inside with his trademark footwork and landed flush? We’ll never know, but the thought still gives me goosebumps.

That raps up my dream Manny Pacquiao fights list.

See also – Why Boxing Still Needs Manny Pacquiao As Of 2016