Other than the obvious fact that it's been nearly 15 years since they last saw their team lift the league trophy, they have also had to see Arsenal, Manchester United and, more recently, Chelsea surge ahead as the teams to beat in England.
And there have been a few false dawns during that time, most notably when Gerard Houllier guided the Reds to five trophies in 2001, and then leading them to second spot in the Premiership the season thereafter.
But rather than closing the gap on the leaders, the daylight between them has become considerably more, with the Merseysiders finishing a massive 30 points behind champions Arsenal last season.
The Reds powers-that-be's work in the transfer market has often been cited as a contributing factor to the club's lack of success, having seen massive investments in the likes of Emile Heskey (£11m) and El-Hadji Diouf (£10m) end in relative failure.
However, the capture of Harry Kewell from Leeds at the beginning of last season was hailed as a massive coup with the winger's arrival to be the final piece in the puzzle.
The Australian, snapped up for a cut-price £5million when valued at over £30million just a year earlier, rejected the overtures of Manchester United and Chelsea to sign for his boyhood idols.
While the Reds had sorted out their leaky defence from previous seasons, the attacking part of their game was still lacking and Kewell was touted as the one to unlock the defences and provide the ammunition for Heskey and Michael Owen to do what they (supposedly) do best.
After all, during his time at Elland Road he had established himself as one of the premier wide players in world football, with clubs in Spain and Italy having also eyed his progress.
A record of 60-odd goals in just over 200 starts for the Whites bore testament to his undoubted talent, with the strikes more often than not ending up as Goal of the Month and Season nominations.
Hence then, the Liverpool supporters' frustrations at what the 26-year-old Australian has delivered during his 14-month stay at Anfield.
Seven league goals in his first season was well below what was expected of him. And it's gone downhill from there...
It's now nine months since Kewell last scored in any competition and, to be frank, it doesn't look like this run will end any time soon.
Not only is he bereft of any shred of confidence, but also appears to be packing a few extra kilos as well.
The fact that some people suggested he had a good game in the 2-1 win over Arsenal on Sunday just goes to show how expectations surrounding the winger has dropped. Fair enough, he worked hard for the team, but a performance like that in which he constantly gave the ball away and looked well off the pace would have been met by some surprise during the glory days at Leeds.
And can you even remember the last time he managed to take on a player and beat him? For goodness sake, even David Beckham managed to dribble past a player on Sunday night.
So now, with Liverpool facing a striker crisis of note with Djibril Cisse, Milan Baros and Luis Garcia out injured, it's time for the Aussie to stand up and be counted and be the man to lead the mini-revolution at Anfield.
Either that, or he can prepare himself for some bench time when Rafael Benitez finally has all his first-team players back in action.
BY Ed Gossard