It was 19 years ago when the Whites dropped out of the Premier League, before seeing one of their star man jumping ship to join fierce rivals Manchester United.
Alan Smith was the beating heart of Leeds' side ever since bursting through the academy set-up and becoming a first team star.
Having scored 54 goals in 224 appearances for his hometown team, the striker was well on the way to becoming a club legend - at least that was the case until Sir Alex Ferguson called that summer.
Speaking to the UTD podcast, Smith said: "There had been talk about me signing in January and I spoke to Sir Alex Ferguson about it. But I couldn't sign in January because I wanted to keep Leeds up.
"United went and signed Louis Saha from Fulham, so I just thought my move was dead and buried, and that they wouldn't want me.
"I was at home at the time and Sir Alex rang and I made my decision there and then without consulting anybody else.
"I don't want to make any excuse for signing for Manchester United because it was a football-based decision. From the club's [Leeds] point of view, it was financial. I'd be doing myself a disservice if I didn't sign for, arguably at that time, the biggest club in the world."
Man United completed the deal in the summer of 2004, with Ferguson hailing Smith for his 'special determination' and 'desire', which can't have been good to hear at Elland Road.
Originally a striker, Ferguson's masterstroke came as he retrained Smith into a central midfielder as a replacement for outgoing United legend Roy Keane, a role that he filled successfully in the majority of his 93 appearances at Old Trafford.
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But while Smith's start to life in Manchester went well, Leeds' supporters weren't too pleased as they called the former boy wonder 'Judas' while they adapted to the challenge of life in the Championship.
"For me, it wasn't even a rivalry anymore. If you're not in the same league as someone I don't understand how it can be," Smith said.
"I'd been there from 10 years old, so it was big for them that I chose the destination that I did. But as I look at it, they should be proud of one of their own young players going on to whatever destination it was, in terms of the calibre you go to.
"That should not be forgotten because it's a Leeds-Man United rivalry. I think it didn't really bother me because it was a decision I made purely based on the good of Leeds financially and myself footballing wise."
In the years that followed, Leeds legend Peter Lorimer revealed that, of the interested clubs, Man United were the only ones prepared to pay the transfer fee in full, rather than spread out payments, which was a massive help to the finances.
"Leeds fans didn't want him to go there but as far as the club is concerned, Alan Smith going there probably saved us from going into administration or liquidation a lot earlier than we did," he said
Smith added: "I was a kid when Eric [Cantona] went to Man United and I was probably one of those throwing stones at the team bus when he came!
"The characteristics of both clubs are very, very similar in terms of the beliefs, the history of the clubs, the people who are involved in it, the styles.
"The passion of the fans is very, very similar. I think that's why it made my transition quite easy in that first year. And you're surrounded by world-class players, which makes it a little bit easier as well."