Their paths famously crossed as players on the big stage.
Rewind 17 seasons, as third-tier Chesterfield almost caused an FA Cup sensation by reaching the final at the expense of an expensively-assembled Premier League Middlesbrough side.
Tomorrow, they cross swords as managers, both going for the big prize again, only this time competing as promotion rivals.
Sean Dyche captained the Spireites side - including Clarets goalkeeping coach Billy Mercer - who led Boro - Festa, Emerson, Ravanelli, Juninho et al - by two goals at Old Trafford before eventually drawing 3-3 after extra-time.
He actually scored from the spot to make it 2-0 on the hour, before Boro fought back to earn a replay after extra time.
One man missing from Bryan Robson’s side at Captain Fantastic’s old stomping ground was now-Leicester boss Nigel Pearson.
Pearson was ruled out of the first meeting with an ankle injury, but he returned for the replay, at his former club Sheffield Wednesday’s Hillsborough ground, and the rest was history.
Boro were tighter at the back with his influence and won 3-0, before going on to lose the final against Chelsea.
Dyche looked back: “I remember he missed the first semi-final, and came in for the replay and made a big difference.
“He was a very good player.”
Pearson has since built an impressive CV in management, helping guide Leicester to the League 1 title in 2009 in his first stint in charge, and Dyche added: “I don’t know Nigel that well, only from what we do and in passing, not particularly well on a personal level, but on a professional level yes.
“I last bumped into him in the summer in Portugal on a rather nice golf club. I was playing for charity, he was holidaying.”
And he looked forward to tomorrow’s clash with Leicester at the King Power Stadium: “We’ve got ourselves back in that top spot again. Leicester have had two awkward results - we know that can happen and we know how tough the Championship is. Nigel does as well.
“I’ve been happy with the consistency, the performances have been good. You can’t guarantee every game’s a win, although we’ve made a good fist of it so far that’s for sure.”