He won five trophies with the Blues during that time and was a team-mate of Roberto Di Matteo - the Italian who was sacked as their manager just six months after winning the Champions League in May.
Like most in football he was shocked to see Di Matteo lose his job but, having been a Chelsea player when both Ruud Gullit and Gianluca Vialli lost their jobs at the hands of current Leeds chairman Ken Bates, he accepts such occurrences are part of the London club's make-up and believes recent changes could play into Leeds' hands.
"I have to say, I thought it was a big shame when Roberto left, he is a good friend, a very good manager and I thought it was way too early to push him out of the door," said Flo, who this year turned out for Sogndal at the age of 39.
"But that's just the way it is at Chelsea. They change their manager a lot.
"Their game with Leeds is going to be very exciting. Chelsea have had some problems lately and that could be a factor."
Di Matteo was replaced by Rafael Benitez, whose appointment has not gone down well with those who used to idolise Flo on the Stamford Bridge terraces, with Sunday's Club World Cup loss to Corinthians merely adding to the sticks they can beat the Spaniard with.
Flo can see why Benitez has had a tough initiation, but believes the League Cup gives him a chance to get his hands on some silverware. "It's a difficult job for him, because Di Matteo was really popular with all the fans there," he added.
"But this is a great chance for them. It's still a great cup and you can see the enthusiasm in the Leeds supporters for it. It's a really big game and it's another step closer to the final if you win, which he (Benitez) will be looking at."