It's in our nature as football fans to compare players of any era to the current teams and superstars of today.
Heskey spent four years at the Merseyside juggernaut, and experienced immediate success off the back of his stint with Leicester.
Winning trophies, playing good football and having a unique squad were the elements for Liverpool's success during Heskey's time and the same could be said for the current lineup at Anfield.
He admits that the current Liverpool squad have experienced more highs and are more likely destined for greatness than his team ever was.
"If I had to compare, it's genuinely hard to define but they are probably ahead of us," Heskey admitted.
"They've gone to two UEFA Champions league finals, and they narrowly missed out on the league by one point. They're the kind of heights we could have only aspire to, and Jurgen Klopp has done a fantastic job with recruiting and imposing his style of play."
With the advancement in technologies, elite performance and player welfare, football is a very different landscape these days to those of the late 90's and early 2000's, yet there are fundamentals that can be contrasted to highlight the distinction between eras of football.
"If we're talking about specifics between the two, their style of play is much more aggressive and explosive," Heskey continued.
"You don't have to look far to see they're always on the front foot and looking to exploit their opponents in all areas. They impose themselves from the opening whistle, whereas back in my day we sat back a lot and chose to hit them on the break, attacking from our defence."
The Dutch defender holds the height advantage over the former England striker, and would've posed a fantastic competitor in all aspects of Heskey's game.
"I would've loved the challenge, he's a brilliant defender. I would've tried to challenge him in every area, whether he's quicker than I was, or physically stronger. If not, I would've tried to figure him out in a more methodical way.
"A lot of young footballers these days look to the manager how to change the game, but I would look internally for the answers from myself. Heskey vs van Dijk would have been an amazing match up."