At the Hoops' hotel in Moscow a local journalist, in the most offbeat way, engaged the bemused Parkhead boss in discussion about various topics including Rangers, Sir Sean Connery and former Celtic midfielder Aiden McGeady, who now plies his trade for the Russian outfit, before a UEFA official eventually stepped in to prevent it all becoming too silly.
The Northern Irishman posted on his Twitter account afterwards "Well that was one of the more bizarre press conferences I've had to do."
Previews of other Champions League Tuesday fixtures
Lennon was asked if he would help Old Firm rivals Rangers, who relaunched in the Irn-Bru Third Division this season after descending into administration, if he had 100million euros to spend.
The former Celtic skipper jokingly responded: "Would I help Rangers? If I had that money you wouldn't see me again, I would be in Las Vegas or somewhere like that.
"I have no idea how I would spend the money, I would invest it in the club and team and keep a little for myself."
Lennon was also asked, on the theme of benevolent club presidents and owners, if he would approach Sir Sean Connery if Celtic had any financial problems.
Almost incredulous at the random link between the Scottish actor and the Parkhead club, he replied: "You've done your homework, haven't you?
"We don't see us having too many financial problems. The club is run very well and we have to work within our means.
"We don't have the finances of English clubs or a super-rich owner who is quite happy to plough loads of money in.
"We run the club as a business, we have a budget and a strategy set and we work within that and it has been very successful for us in terms of building a team for the future - but if you have Sean Connery's number I will take it off you."
Lennon - who at one point asked the UEFA interpreter of his Russian inquisitor, "is he a real journalist?" - was asked if a monument should be built in honour of McGeady for earning the Parkhead club a reported £9million when he joined Spartak in 2010.
"A statue?" said the Celtic manager.
"You need to do a little bit more at a club like ours to get a statue. Only people like Jock Stein and the great Jimmy Johnstone are worthy of that so far.
"Aiden is a tremendous player, very talented and definitely one to watch tomorrow [Tuesday] and I'm sure he will be even more motivated than usual against his old club."
McGeady himself admitted he will have to contend with mixed emotions at facing his boyhood heroes.
"It'll be the first time I've faced Celtic," he told BBC Scotland.
"I try to catch most Celtic games on TV and I keep up to date with what's going on online. But, obviously, I'm now a Spartak player.
"Of course, Celtic are the team I grew up with, the team I support and the team I grew to love, but tomorrow night that all goes out the window."
McGeady was rested for the 3-1 win over Amkar at the weekend which took Spartak to fifth in the Russian Premier League, four points behind leaders Anzhi Makhachkala.
Spartak are looking for their first points in Group G, though, after losing 3-2 away to Barcelona in their opening game as the Scottish champions played out a goalless home draw against Benfica.
The Scotland-born Republic of Ireland player believes the artificial pitch at the Luzhniki Stadium maybe be a factor tomorrow night.
He added: "Generally, our record over the past few years hasn't been that great at home, but, possibly, Celtic aren't used to playing on this type of pitch [artificial surface], so it's possibly going to be a tricky match for them.
"It's going to be an exciting game."