As much as David O’Leary’s side from the turn of the millennium are rightfully celebrated, one aspect of that period sticks out like a sore thumb.
Quite simply, they did not win anything of note, and that will remain a stick with which to beat them forever.
Maybe it is not the Leeds United way to win trophies. After all, the club’s entire haul of trophies in the FA Cup can be counted on a single finger.
Don Revie’s team were great, undisputably one of the best teams in Europe, but they reached four times the number of FA Cup finals they won.
Maybe O’Leary’s own issues in England’s most prestigious cup competition are incomparable, with the Irishman never leading Leeds to a final in any competition, unlike Revie’s repeat losses in the most unfortunate of circumstances.
Famously, O’Leary’s side exited the competition in the third round against Cardiff City in 2001 having predicted they would be revisiting the Welsh capital at the end of the season for the showpiece final.
However, a similar struggle two years prior is rarely mentioned when Leeds’ displays in the cup from that entire period are discussed.
Leeds were forced to a replay by Conference side Rushden and Diamonds after being held to a 0-0 draw at Nene Park. In part that was the result of a crippling list of injuries, but even so there was disappointment that Leeds had to host their non-league opposition at Elland Road to earn progression.
After only 11 minutes of the replay, the situation seemed to have worsened.
The returning Lucas Radebe was outpaced by Miguel De Souza, the South African clearly struggling for fitness after a spell of five games on the sidelines.
De Souza’s cross was dangerous and palmed away by Nigel Martyn.
It fell to Carl Heggs, who saw his effort hit the post, and then Heggs struck the rebound straight into the bottom corner, sending the travelling fans into ecstacy.
Leeds were not behind for long. Alan Smith, then a young prodigy on his way up, scored his first ever FA Cup goal with only 22 minutes on the clock to bring the tie level.
The 18-year-old was sent clean through on goal by Jimmy Floyd Hasselbaink and made no mistake, despite being confronted by Diamonds’ 6ft7 goalkeeper Ian Feuer.
Shortly after half-time the tie was flipped on its head, Leeds and Smith scoring their second.
Harry Kewell combined with Hasselbaink, who teed up Smith once more. As was clearly becoming his way, the Thorp Arch graduate emphatically powered home to put the Whites into the lead.
From there what had seemed a tricky tie became simple.
Where De Souza and Heggs missed a pair of opportunities, Hasselbaink did not.
The Dutch international wrapped up the game with a drilled finish, the third for Leeds and a goal that ensured that their name was in the hat for the fourth round.
That saw a victory against Portsmouth away from home, the young side destroying Pompey 5-1.
The fifth round brought Tottenham Hotspur to Elland Road.
A draw and a replay later, Leeds were once again eliminated, silverware as conspicuously absent as ever.
Leeds United 3
(Smith 22, 52; Hasselbaink 67)
Rushden and Diamonds 1 (Carl Heggs, 11)
FA CUP THIRD ROUND REPLAY JANUARY 13, 1999
Leeds United: Martyn, Wetherall, Radebe, Woodgate; Harte, Hopkin, Bowyer, Kewell, Granville; Smith (Haaland, 85), Hasselbaink.
Rushden and Diamonds: Feuer, Wooding, Bradshaw, Rodwell, Underwood; Hamsher (Brady, 75), McElhatton, Butterworth, Heggs; Foster (West, 45), De Souza (Whyte, 88).