Success-starved Leeds fans have had to content themselves with memories of the great sides of yesteryear when their trips to Anfield were headlined as the match of the day.
Former Leeds winger and manager Eddie Gray was at Elland Road on Monday to help preview the game for LUTV and recalled such games as the 1965 FA Cup final and the goalless draw at Anfield in 1969 that clinched Don Revie's side the old Division One title.
More recent clashes featured Tony Yeboah's stunning volley at Elland Road in 1995 and Mark Viduka's four-goal haul in a 4-3 win against Liverpool in 2000.
"It's a historic fixture in English football and we have to respect that," said Monk.
"We're under no illusions. It's a very difficult game for us, they're an extremely talented side, they're doing very well in the league and obviously one of the better teams across European football.
"It's a great challenge, that's how we have to look at it. Our young players have a bit of freedom to go there.
"We're under no pressure, the odds are against us, but we have good belief in ourselves.
"It's important these players go through this type of experience because if you want to progress and get to the highest level of football - staff and players - we have to embrace this type of challenge and the atmosphere we face tomorrow."
Monk, the latest head coach to take up club owner Massimo Cellino's precarious challenge, has steered Leeds to fifth place in the Sky Bet Championship since replacing Steve Evans in the summer.
There are genuine hopes among Leeds fans that Monk has already instilled the organisation and culture required to climb back to the top flight and the former Swansea boss is keen to showcase his side's improvement on the biggest stage.
"What we're trying to do here, and of course we're a new group to those from years before, we're trying to fight for that right to get back there and get these fans back to the level their support deserves," he said.
"There's a long way to go and a lot of improvement to go, but this type of challenge coming along the way like tomorrow night is another step in the right direction.
"These are the type of nights we want to give our fans more often and they're the ones the players want to fight for more often."