It has been reported today that Lennon has returned to training with Spurs and is not far away from making a return to full fitness.
However, where exactly will the player fit in? Since Gareth Bale's departure, manager Andre Villas-Boas has signed a clutch of players in the hope that their collective prowess will be enough to match Bale's loss.
These new signings have already given Villas-Boas a selection headache, it is clear that the manager is yet to discover what his best lineup is.
Lennon now has a number of competitors for his wide position on the right, including Erik Lamela and Andros Townsend. Also able to start in Lennon's position are Gylfi Sigurdsson, Lewis Holtby and Nacer Chadli.
To make his life even harder, the England winger is coming back from an injury, and is therefore at a disadvantage for the simple reason that he has only played one game this season.
Other fitter players have been at the forefront of Vilas-Boas's mind, Lennon now has to remind his manager that he should be starting ahead of a number of good wide men.
One of Tottenham's most impressive performers this season has been Andros Townsend. He has shown remarkable drive to stay at Tottenham after being sent out on loan on nine separate occasions.
Having just nailed down a starting place at his parent club for the first time in his career, he is not going to give it up easily. It's quite obvious that the player has been buoyed by the faith that his manager has shown in him.
Lennon also needs to develop an on-field relationship with all of Spurs' new players, something that will be very difficult if he does not get on the pitch to prove himself.
Undoubtedly, his first opportunity on returning from injury will be coming from the bench, he needs to prove to Villas-Boas that he is worthy of starting.
Yet, he will also be battling against a number of very expensive players, players who are also itching to prove themselves.
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