Harry Redknapp's side bowed out of the UEFA Cup despite a brave attempt to over-turn a 2-0 first leg deficit against Shakhtar Donetsk at White Hart Lane in the Round of 32.
Giovani Dos Santos scored his first goal for the Club to give us hope in the second half, but Fernandinho's late strike equalised on the night to give the Ukrainian champions a 3-1 aggregate victory.
As expected, there were no less than 10 changes to the side that beat Hull in the league on Monday, with two notable introductions in particular.
Jon Obika followed in the footsteps of Under-18 team-mate Dean Parrett the week before by making his first start for the Club up-front alongside Fraizer Campbell.
Meanwhile, Jamie O'Hara returned to action after a month out with a hip injury, while Tom Huddlestone captained the side for the first time.
It was always going to be a tough ask to over-turn a two goal deficit against a strong Shakhtar side, and our young team spent much of the opening exchanges getting to grips with their opponents.
Brazilian midfielder Fernandinho seemed to provide their main threat, forcing Heurelho Gomes into a full stretch save from 20 yards on as many minutes.
Gilberto, making his first start since December, then blocked Fernandinho's header from Dario Srna's corner on the line on 27 minutes, before the same player was allowed to flash a free header across goal from the resulting set-piece.
That seemed to spark us into action. On the half hour mark, there were strong claims for a penalty when Campbell appeared to be shoved over in the box by Razvan Rat.
Then 18-year-old Obika had his first sighting at goal with a good effort from 25 yards that flew only inches wide.
In the same spell of pressure, we once again left referee Paolo Tagliavento with a decision to make when Campbell went down in the box for a second time under Fernandinho's challenge. But again appeals were turned down.
Although Gomes was forced into another save by Rat on 35 minutes, the best chances of the half fell to us.
On 39 minutes, O'Hara played a ball into Obika who turned and shot just wide from inside the box.
Two minutes later, Huddlestone picked out Gareth Bale with a pinpoint pass from the back. The Welshman cut inside Srna into the box but could only fire his shot straight at goalkeeper Andriy Pyatov on his weaker right foot.
Then Pascal Chimbonda came up from the back to again test the goalkeeper with a header from Chris Gunter's cross as we finished the half the stronger side.
Our dominance continued into the second period as Obika was only inches away from connecting with Bale's ball across goal in the opening minute.
But 10 minutes in we took the lead on the night. Bale played a ball into Campbell which the striker turned neatly into the path of Giovani who ran onto it and smashed a terrific shot left footed into the roof of the net.
The 19-year-old had finally broken his duck after 11 attempts since joining from Barcelona last summer.
Now we were looking for an equalising goal to take the tie into extra time, and our effort in attempting to do so cannot have been faulted.
Just minutes after Giovani's strike, Gilberto linked up with Bale on the left hand side and fired a ball across goal which nobody could get on the end of.
Then came the most controversial moment of the match. Campbell got in between two defenders to receive a Huddlestone ball before having his legs taken from under him by Mykola Ischenko inside the box. But again, appeals were waved away by Tagliavento.
It would have been the least we deserved as Shakhtar had offered little going forward, and Gomes was equal to it when they did.
On 69 minutes, Jadson slid in Marcelo Moreno but the goalkeeper stood up to him well to make the save, and Jadson himself had a volley saved by his fellow countryman eight minutes from time.
But the longer the game went on without us finding that second goal, the more tired we seemed to get, and Fernandinho put the tie out of sight with four minutes remaining.
The impressive Jadson found him on the left side of the box, and his finish was sublime inside Gomes' left-hand post.
The closest we had come to getting an equaliser had been six minutes beforehand when Bale sent a free-kick just wide from the edge of the box, but it was not to be.
Our hopes of silverware this season rest on Sunday's Carling Cup Final with Manchester United at Wembley.
Spurs (4-4-2): Gomes; Gunter, Huddlestone, Chimbonda, Gilberto (Bostock, 77); Giovani, Palacios, O'Hara (Parrett, 71), Bale; Obika, Campbell
Subs not used: Jansson, C Butcher, Smith, Mason, Townsend
Shakhtar (4-4-1-1) Pyatov; Srna, Ischenko, Chygrynskyy, Rat; Ilsinho (Gay, 80), Fernandinho, Lewandowski, Willian (Hubschman, 46); Jadson; Gladkyy (Moreno, 61)
Subs not used: Khudzhamov, Duljaj, Kucher, Sleznov