But the Hoops boss knows it is not possible for the same thing to happen for a third time because they cannot be drawn against Barcelona in Nyon tomorrow.
The Parkhead club were eliminated from the tournament in season 2006-2007 when AC Milan finally put them to the sword in extra time – thanks to a wonder goal from Brazilian superstar Kaka in the San Siro – before going on to win the competition.
Having managed to defy all the odds by progressing from their group section for the second year running, Gordon Strachan's side were unfortunate enough to be drawn against Barca who knocked them out back in 2008.
And Lennon said: "I don't think we could have asked for tougher draws on both occasions.
"The first year we qualified under Gordon, when I was still playing, we were drawn against AC Milan and they were a top, top team that year.
"They went on to win the competition which is proof of that. We gave it a great shot but they brought on Kaka and he went on to score an unbelievable goal during extra-time which took them through.
"For me, they were the best side in the competition that year.
"The following year, our reward for qualifying was two legs against Barcelona. Unlike Milan, they didn't go on to win it but I still considered them the best team that year. It was a terribly tough draw.
"If you were to ask me who are currently the best team in the Champions League I'd have to say Barcelona.
"That is the good thing this time around as we can't be drawn against them because we've faced them in the group section.
"But then you look at the other teams we could potentially be drawn against and you realise it is still going to be extremely tough."
Celtic will be drawn against one of the seven group winners with Borussia Dortmund, Bayern Munich, Schalke, Manchester United, Juventus, PSG and Malaga all lying in wait.
Lennon, though, refused to be downbeat.
He said: "How can you pick one of the teams from that list?
"We will just wait and see. It's great for us that we are still in the competition and we'll give it our best shot.
"It would be incredible to go one step further."