A Uefa Cup final appearance in Seville with Celtic was memorable but came when he was approaching veteran status. Winning the League Cup twice with Leicester City were also career-changing moments.
But where he really felt he grew as a player and person was when he was included in the Northern Ireland party to play games against Mexico and Colombia in 1994. Both these sides had qualified for the World Cup in America and Northern Ireland were invited to be part of their warm-up schedule.
Lennon was in his early 20s and still at Crewe Alexandra. One minute he remembers playing at Rochdale, the next he was trying to match the runs of Hugo Sanchez in the blazing heat of Miami. It helped set him up for the successes and challenges, for there were many of these, to come.
“It was a real eye-opener for me,” he recalled. “To see top-quality players just before a World Cup. Both teams were going to the World Cup. You saw the game at the highest level.
“It was a real education. Some of these players now in Scotland could do with going and playing against a Mexican team and seeing top players, in the South American culture, and how hungry they are.”
This is why he won’t stand in the way of Dylan McGeouch, John McGinn or any other Hibernian player selected by Alex McLeish for this summer’s two-game tour of South America. Scotland are scheduled to play Mexico and Peru.
While the games have caused controversy, and helped end Stewart Regan’s reign as SFA chief executive, Lennon says he is fully on board. He believes it’s not necessary to include Celtic players since McLeish will know what they can do. But he hopes McGeouch is among those given a chance to shine.
He is part of a Hibs midfield that is garnering praise at present. John McGinn and the returning Scott Allan perhaps draw much of the attention but McGeouch has been a consistent performer now his injury problems are seemingly behind him.
Lennon probably preferred it when McGeouch was operating under the radar. He accepts he will have a job on his hands to convince him to stay. McGeouch is out of contract this summer and talks on a new contract are continuing,
“That’s a decision only Dylan can make,” said Lennon. “I am sure there will be a few interested parties out there. He has a big decision to make obviously. From my point of view, I want to say his best years are in front of him and he’s maybe best served here. But that’s a decision Dylan will have to make himself.
“Talks are on-going,” he added. “If he keeps on playing the way he is going we might have to go back to him again, make him an offer he can’t refuse!”
Lennon believes that McGeouch is knocking on the door of the Scotland squad. “It’s a big challenge,” he said. “Is he good enough for Scotland? Maybe not yet. He needs a full season under his belt and a good pre-season next year and then we can see…
“I just think it is maybe a bit early to put him in that category, up with the likes of [Scott] Brown. But when he has played against the Browns of this world, the [Kenny] McLeans of this world, he has been as good as anyone. Maybe he could make the squad – I am just not sure he is ready to play a competitive international.”
It’s why Lennon reckons the player will be one of those to benefit from a trip to Central and South America. He doesn’t see the point in sending weary Celtic players who already have experience of playing at the highest level there.
Whether these players finish the season as champions once more remains to be seen. After this weekend’s results, which saw Rangers close the gap on leaders Celtic to nine points and Lennon’s own side draw to within five points of second place, some wonder whether we have a title race on our hands. The Hibs manager believes we do.
“It’s nine points with 12 games to go – so why not?” he said.
“I still think Celtic will win the league. Brendan [Rodgers] prioritised Thursday night [v Zenit St Petersburg] with his team selection on Sunday [v St Johnstone], I get that.
“Actually, they have come out a point better off. They are nine points clear whereas they were eight points clear going into the weekend. It is going to be very difficult for the chasing pack, but why not? You could say there is a title race on.
“Rangers, Aberdeen, ourselves, [but] the teams behind need to find consistency if there is going to be any sort of title challenge at all.”