Deadline Day was only a sign of things to come, however, with boss Mauricio Pochettino now said to be looking to offload the 27-year-old in January.
It is only early days in the Premier League season, of course, but Lennon has just 61 minutes of game time to his name three matches into the campaign, all in just one appearance.
But would Tottenham be right to let the winger go statistically?
|Team||Pos||Assists||Dribbles Won||Accurate Crosses||Successful Final-Third Passes||Apps||Mins|
In terms of goalscoring, Lennon chipped in with just one goal last term and, as Opta stats show, his contribution in last season's Premier League was far from spectacular.
In an average campaign for the north London side, Lennon produced a similar level to a number of Spurs midfielders around him who failed to shine. Assist-wise, Christian Eriksen led the way with eight and the 27-year-old registered five less. He also made just 15 accurate crosses compared to Eriksen's eight.
But the same statistics show that, if anyone deserves to go, it should not necessarily be Lennon - as he was far from his side's worst player. On the ball, for instance, Lennon won 30 dribbles, while he also completed 262 final-third passes.
The problem for the winger under Pochettino is that some of Tottenham's underperformers - prime example, Erik Lamela - are starting to come to the fore now. Lennon's directness out wide, meanwhile, may not render him too suited to the new Spurs boss's preferred style of play.
Overall, then, the wide man may be better suited elsewhere where he can be appreciated for his ability to surge down the byline. But whether Tottenham should sell him is more debatable.
Statistically, Lennon was far from a star performer last season - and yet he still fared favourably compared to many other Spurs midfielders.