Dyche is now in his first year of senior management and looking to use those memories to help his Watford side cause an upset of their own against Tottenham at Vicarage Road.
The 40-year-old former defender scored from the penalty spot to put Chesterfield into a 2-0 semi-final lead against Middlesbrough at Old Trafford in 1997 - and within touching distance of becoming the first third-tier side to reach the FA Cup final.
Boro hit back that day to take the lead before the Spireites salvaged a 3-3 draw after extra-time, only to bow out 3-0 in a replay. But Dyche feels the transformation of the game on these shores since then has made those exploits much harder to replicate.
"The Chesterfield thing was a different era," Dyche said. "Take nothing away from that run but I think that was when clubs were only just beginning to bring in European and world talent - Fabrizio Ravanelli and Juninho and people like that.
"Now I think it's commonplace, the world's become a smaller place when it comes to football, and Tottenham are a good example of that.
"They're now taking players from all over the world and looking for the absolute top level of player they can get and they put massive resources into the infrastructure and into diet, support systems these players now need.
"That's where the gap has got bigger from my time having a run with Chesterfield and playing Middlesbrough, to what it is now with Watford playing Tottenham.
"The gap is a financial gap and the way they go about their business with recruitment is a completely different thing now, so it's become a lot tougher - even for clubs like ourselves and we consider ourselves a reasonably sized club.
"That gap has got bigger and it's harder to close. But we all know the magic and the beauty of the FA Cup and if that magic dust is willing to sprinkle on us then you never know."
He added: "David v Goliath, no-one shouts for Goliath, do they? Everyone shouts for David, so on this occasion we (Watford) are David."
Striker Marvin Sordell will lead the line for Dyche, who has a full-strength squad to select from barring long-term absentees Martin Taylor (broken toe) and Stephen McGinn (knee).
Watford, 18th in the Championship, go into the game against the Barclays Premier League title chasers having lost their previous three league matches.
But Dyche said: "We're at home, where we've been on a nice run having only lost one in nine. "For sure, it's a real tough task, we don't play Tottenham every week but you've got to believe in what you do and I think the players here do.
"It will be a really good challenge for them to try and give a performance against Tottenham and look to try and win it."
Tottenham manager Harry Redknapp will swap the dock for the dugout and his men will be fully prepared to beat Watford despite his absence from training this week, according to assistant manager Kevin Bond.
Bond and first-team coaches Clive Allen and Joe Jordan have been in charge of training at the club's Chigwell base this week while Redknapp has been contesting two charges of cheating the public purse at Southwark Crown Court. Redknapp, who denies both charges, will be available to lead his team out at Watford, however.
Bond was keen to emphasise it has been a case of business as usual at the club this week despite the absence of the manager.
Tottenham coped well when they were without their manager for two weeks in November after he underwent a heart procedure and Bond insists Redknapp's absence has not had any effect on the squad this week.
"Clearly the manager is not here, but (it has had) very little (effect) really," Bond said. "The training carries on pretty much as normal and everybody has been getting on with things as normal so there's not really a lot of difference except obviously Harry is not here during the day.
"He will be at the match and he will pick the team, of course."
Gareth Bale (thigh), Scott Parker (hamstring) and Younes Kaboul (groin) are all doubts, with the likes of Steven Pienaar, Danny Rose and Niko Kranjcar set to get some game time.
Bond added: "Champions League is our number one goal but the FA Cup is hugely important to us. "The players crave a cup final. They crave playing in the big games, the one-off games."
Watford V Tottenham - view commentary, squad, and statictics of the game live.