Competition for places at White Hart Lane inevitably means that a certain number of players that were once deemed as key first-team players outgrow the club.
The likes of Younes Kaboul and Emmanuel Adebayor have paid the price of progress this season, with North London exits seeming highly likely this summer.
The flying winger is the longest serving player on Tottenham’s books, but the emergence of Andros Townsend and big-money addition of Érik Lamela have limited his chances of first-team football at White Hart Lane.
A consistent feature in the Spurs first team since the 2005-06 season, Lennon only made three Premier League starts in the first half of this campaign.
The wideman was part of Spurs’ League Cup success in 2008 and played a considerable part in Tottenham’s solitary Champions League campaign in 2010-11, making appearances in all ten of the club’s European fixtures.
However, with Mauricio Pochettino placing an emphasis on youth and 27-year-old Lennon’s attributes not as keenly relied on, it appears that Spurs are willing to cash in on the England international at the end of the season.
Since his January loan switch, Lennon has impressed at Goodison Park and netted the winner in Everton’s most recent game, a 2-1 away victory at QPR.
With five Premier League starts for the Toffees so far, Lennon has offered Roberto Martínez’s men much more incision in the final third, with his scintillating pace adding to the attributes of Everton’s other attackers.
The Merseyside club had failed to replace impressive loan star Gerard Deulofeu after a successful temporary stint at Goodison last season and although the respective wingers’ skillsets are different, Lennon certainly adds quality to Everton.
Spurs meanwhile have chopped and changed on their right flank this term, with Lamela, Townsend and Nacer Chadli taking it in turns to try and establish themselves as the preferred option.
Chadli has suffered a dip in form in recent weeks but is most commonly deployed on the left flank as an inverted winger.
The youth-team graduate burst onto the scene last season with some scintillating early displays, but his accuracy has dropped significantly over the last 12 months.
With opposition defenders wise to his ploy of cutting in-field and his final delivery persistently lacking, a section of the White Hart Lane faithful have called for Townsend to be upgraded this summer.
His presence in the England squad seems a peculiar choice by Roy Hodgson, who has seemingly picked the winger on past exploits rather than current form.
Lamela has shown fleeting glances this season of why he was so highly rated in Italy, while it has to be said that he has an eye for a pass and is working harder to track back in recent months.
However, the Argentina international still appears lightweight, coughs up possession too frequently and has limited influence over proceedings for prolonged periods.
As such, sorting out the right wing berth will be one of Pochettino’s priorities this summer – some Spurs fans are calling for the introduction of another youth team player next season, Alex Pritchard, who has been starring on loan at Brentford.
That said, the casual disregard of someone with Lennon’s considerable attributes must be deemed as a mistake by the North London club.
This is only perpetuated by the fact that the 27-year-old is excelling at Goodison, while Townsend in particular cuts a forlorn and highly frustrating figure.
Lennon’s presence in Pochettino’s options would offer an experienced player that looks a lot more viable than the two current major options.
For Everton, capturing the winger on a permanent deal could well be a canny piece of business, as getting the best out of Lennon would see them possess arguably one of the most devastating widemen in English football when on form.