Lennon had a prolonged stint on the sidelines with a groin injury and failed to shine at the World Cup with England or during Tottenham's start to the current campaign. The 23-year-old did not make Fabio Capello's squad for the recent qualifiers with Bulgaria and Switzerland.
Now Redknapp must decide whether to play Lennon despite his slump in form or play Dutch playmaker Rafael Van der Vaart out wide instead. But regardless of his team selection against Dutch champions FC Twente, Redknapp is certain Lennon will eventually come good.
"He's had the injury and he had a quiet World Cup, really,'' Redknapp said. "I think he's getting over the injury from last season. But he's a matchwinner on his day and it's very hard to be consistent when you play out in that wide position, when you've got to beat people every week and people expect you to get the ball and go whizzing past full-backs, cross balls.
"Full-backs now are as quick as wingers, they get tight, they stop you getting the ball. You've got to work very hard to get on the ball now when you play in that wide position. It's not always easy but he'll come good.'
"He's a quiet little lad. But one game can turn it all for him. He just needs to get a bit of confidence. Maybe in training you work with him and you stick somebody at left-back who you're confident that he can get by. I'll find one!'''
Fellow midfielder Tom Huddlestone believes Lennon is suffering from being double-marked by opponents this season. "I think a lot of teams know his qualities,'' said Huddlestone, who could captain Spurs on Wednesday.
"At the West Ham game at the weekend, he had a left-back against him and [Luis] Boa Morte - even though he played left-wing - didn't really get forward that much. It was sort of a doubling act on Aaron. Anybody with two players on them is going to find it difficult.''
Lennon's impact has been overshadowed by team-mate Gareth Bale, who is currently in a rich vein of form. Bale has operated in a left wing role in many of Tottenham's games but Redknapp says the Welshman will eventually settle into a left-back role.
"I think in years to come, he'll be the best left-back anywhere. But he's also a great left-sided player and it suits me to play him wide left most of the time because [Benoit] Assou-Ekotto is also a top, top-class left-back.''
Despite his concerns over Lennon, Redknapp's real worry for the game with Twente lies at the back, where he has just one fully fit recognised centre-half in Sebastien Bassong. He may risk captain Ledley King, but if not, Vedran Corluka will continue in the heart of defence.
"The biggest problem you have is probably getting the players up for the Premier League games after the Champions League,'' said Redknapp, whose side have won just two of their six league matches this term.
"You have to juggle around your team, I've found and when you keep changing your team, it makes it difficult to get continuity. We've had to do that an awful lot - change the team - probably through injury more than anything, especially in the back.
"It's a tight group,'' he added. ''Every point is going to be very vital. I think we need to win our home games; obviously, if you do that, you'll qualify. So tomorrow's a massive game for us; it's a game we need to win.''