Victory against West Ham in their final Premiership game next Sunday will guarantee a top-four finish and a season to remember for the players and backroom staff at White Hart Lane.
Lennon, who turned 19 last week proved the difference for Spurs once again with his amazing burst of pace and he showed the other side to his game when he scored a fantastic goal to secure a priceless three points for the home side.
The timing could not have been better as England coach Sven-Goran Eriksson was sitting in the directors box and must be contemplating how he is going to survive without the injured Wayne Rooney at the World Cup this summer.
Bolton had European dreams of their own and knew a victory at White Hart Lane would give them an outside chance of getting into the UEFA Cup.
Sam Allardyce's side came into the game brimming with confidence following their 4-1 win over Charlton last weekend and it certainly showed in the opening 45 minutes as they dominated the game.
Tottenham looked anything but a team pushing for a place in the Champions League, as they failed to create a clear-cut opening and were fortunate to go in at half-time on level terms.
The home side certainly had luck on their side on nine minutes Hidetoshi Nakata saw his close-range shot come back off the post.
Jared Borgetti nodded the ball into the path of the Japan international who struck a fierce drive which looked destined for the back of the net.
The ball beat Paul Robinson in the Tottenham goal, but the ball came back off the inside of the post and away to safety.
Bolton continued to mount pressure on the home goal and Ivan Campo should have broken the deadlock on the half hour mark.
Gary Speed's long throw-in was flicked on by Kevin Davies into the path of Campo, but the Spanish midfielder fired his close-range shot over the crossbar.
Michael Dawson then came to the rescue of Tottenham on 40 minutes when he cleared Stelios Giannakopoulos' shot off the line.
Jol must have said some strong words during the half-time interval because Tottenham looked a completely different side in the second half.
Even without the injured Robbie Keane, who was forced to withdraw from the action with a twisted ankle, Tottenham started to show the form which has made them Champions League contenders.
Dawson's shot on 48 minutes was cleared off the line by Ricardo Gardner, while the ever impressive Lennon burst past two Bolton players on 51 minutes and fired the ball just past over the bar.
But the talented winger got his just rewards on the hour mark when he fired thecrucial match-winner and it could prove to be the gateway into the Champions League.
Michael Carrick picked out the former Leeds winger inside the box and Lennon made no mistake striking a powerful shot past Jussi Jaaskelainen into the corner of the net.
Bolton had strong claims for a penalty turned down on 75 minutes. Stelios appeared to be brought down inside the box by Dawson, but referee Alan Wiley waved for play to continue, much to the fury of the Bolton players.
Tottenham held on and must now be praying that Barcelona can do them a big favour when they play Arsenal in the Champions League final on May 17.