Eight times he has faced Celtic since becoming St Mirren manager in the summer of 2010 and eight times his team have lost. They have barely left a scratch on Celtic in that two-and-a-half year period, conceding 22 goals in eight matches and not managing a solitary strike in return.
It is the sort of record that would leave most managers cowering under their desk ahead of a ninth, and most significant, meeting but Lennon's cup continues to overflow with positivity. His is a stoicism and perseverance on a par with Robert the Bruce's fabled spider.
St Mirren would be underdogs in a cup semi-final against Celtic regardless of circumstances but the size of their task in the Scottish Communities League Cup at Hampden on Sunday is made even greater by that dreadful record. Throw in their respective form – Celtic have scored eight goals in their last two league games, St Mirren lost 4-1 to Ross County at home last weekend – and it would surely rank as one of the biggest shocks of recent times were the Paisley side to somehow secure a safe passage through to the final.
Lennon acknowledges the enormity of the challenge but is not deterred by it. His inspiration stems from the various upsets that football throws up from time to time, most recently Bradford City's march to the Capital One Cup final. "Celtic have turned us over on numerous occasions but, with it being a one-off cup game, anything can happen," he said.
"In a lot of people's minds, it would be a miracle if St Mirren were to beat Celtic. But you just have to look at Chelsea last season when they beat Barcelona and Bayern Munich to win the Champions League; Kilmarnock beat Celtic in the final of this tournament last season; Arbroath took Celtic through 180 minutes of [William Hill Scottish Cup] football and narrowly lost 1-0; Bradford got to the final of the Capital One Cup by beating Aston Villa so I am a big believer in miracles. And if we are prepared to work and have that confidence and that bravery, I certainly believe the underdog can have their day."
St Mirren have not been at Hampden since they lost the 2010 final to Rangers but there are none of the usual platitudes from Lennon about his players "enjoying their big day out" or "playing with no pressure or expectation".
"We will certainly not be going there to enjoy the occasion," he insisted. "We will be going to make it an occasion. We have to go with belief, bravery and confidence if we are going to progress. This is why we fall in love with football, to play in occasions like this and go and win trophies regardless of what level you are at. We are all dreamers and there will be a lot of players taking the field trying to fulfil that dream."
Lennon can speak with the privilege of experience. He was a key figure when Raith Rovers, then of the first division, caused one of the biggest upsets in Scottish football history by lifting the Coca-Cola Cup in 1994. Injury denied him a place in the final but he made a telling contribution in the semi-final, when he converted the decisive penalty to defeat Airdrieonians in a shoot-out.
"I still felt part of the group because I scored a few goals in that competition," he recalled. "I scored the fifth penalty in the semi-final win over Airdrie and scored against St Johnstone in the quarter-final up there. But that profession I was in as a player has now gone. I am a young manager trying to make a new career and it is going along nicely. I am at a fantastic club and we are going to Hampden on Sunday so we can write another chapter in our proud history."