Ex-England striker Heskey enjoyed a successful four-year spell on Merseyside and collected medals in the FA Cup, League Cup and UEFA Cup before departing for Birmingham City at the end of the 2003-04 season.
Further spells at Wigan Athletic and Aston Villa followed, but it appeared unlikely he would line up against Liverpool again when he joined Newcastle Jets in Australia's A-League in September 2012.
However, the 37-year-old forward was handed a return to English football by Championship side Bolton last month and a dream Cup draw duly followed.
And Heskey is hopeful of a warm reception when he takes to the field against Brendan Rodgers' men this weekend.
"It's a wonderful thing to go back," said Heskey.
"I'm 37, I'm not a young lad so to go back and play at Anfield is a great thing. It wasn't long ago, a few months ago, when I was doing work for LFCTV so to actually be going back there and putting my boots on and playing against Liverpool is wonderful.
"I've thought about it. The fans were wonderful to me while I was there. I'll hopefully get a good reception and play my heart out."
If Heskey can help Bolton, who have lost just once in their last 12 matches in all competitions, pull off a surprise then it could potentially deny former team-mate Steven Gerrard a fond Liverpool farewell.
The Liverpool captain is to join MLS side LA Galaxy in July and the date of the FA Cup final falls on his 35th birthday.
Speaking about Gerrard's decision to leave Liverpool, Heskey added: "I believe he's probably leaving maybe a year or so too soon.
"But he's probably weighed up the options, looked at everything and thinks right now is about the right time."
Beating Liverpool will be no easy task considering their resurgence in recent weeks.
After a shaky start to the campaign, Liverpool are on a nine-match unbeaten run and were unlucky to only take a 1-1 draw from Tuesday's League Cup semi-final first leg against Chelsea at Anfield.
Rodgers, who confirmed striker Daniel Sturridge is not yet fit to start as he recovers from a long-term thigh problem, is hoping to use cup competitions as a springboard for another shot at the Premier League title next season.
"The squad needs that time to evolve and work together," he said. "This squad has Premier League winning capabilities.
"If we can get success in a cup competition this year it'll give us greater stimulus to stick together. But you always need more quality."
