Kasey Keller's heroics couldn't prevent penalty heartache as we bowed out of the Carling Cup on Wednesday night.
The American goalkeeper made stunning saves in the final minute of both normal and extra time and then pulled off what looked like being the crucial stop in the penalty shoot-out as this quarter-final went to the wire.
But the joy of keeping out what would have been Gaizka Mendieta's winning penalty soon turned to pain as Mauricio Taricco struck the post with our next kick.
That meant Kasey had to repeat the trick but there was no stopping Frank Queudrue's spot kick and Middlesbrough went through 5-4 in the shoot-out after the tie finished 1-1 after extra time. Gus Poyet also suffered agony from the spot.
The drama of the penalties shouldn't wipe out the fact that we were just five minutes away from a place in the last four.
Darren Anderton put us ahead in the first minute and we held that advantage until the 85th when Michael Ricketts pounced from close range to take the game into extra time.
Anderton was outstanding as we flew out of the traps again in the first half. He pulled the strings from midfield, finished well to open the scoring after Colin Cooper's slip and turned provider for our other notable chance of the first period, Ledley King's header brilliantly tipped over by Schwarzer.
Michael Ricketts should have levelled just before the break and although Boro came more into the game in the second half, we certainly held the upper hand in terms of possession with Robbie Keane and Fredi Kanoute a constant threat.
It took the visitors until the 81st minute to carve out a serious chance - Keller spreading himself to deny Juninho from close range - but they capitalised when their next opportunity knocked.
There was a little luck involved as Steve Carr and Ricketts went for George Boateng's cross and the ball dropped down nicely for Ricketts to make no mistake from six yards.
Keller then produced what must be the save of the season to deny Ricketts in injury time, somehow getting a hand to and then managing to tip over the striker's header from point-blank range.
The game remained in the balance in extra time although Boro now carved out the better chances - Downing volleyed a foot wide, Ricketts started to wheel away in celebration but had actually missed the target from six yards and Juninho failed from 10 yards.
Ricketts and Juninho then missed Boateng's cross and, with time just about up, Keller somehow saw enough of Downing's rocket through a crowd from 18 yards to palm it aside.
So onto the shoot-out. The first six were successful before the first save, Schwarzer keeping out Poyet's effort to his left. Mills and Kanoute scored to leave Mendieta to win the game only for Keller's strong right hand to keep out his low effort.
But Taricco hit the post with Schwarzer having dived the other way with the 11th penalty and Queudrue was left with the chance to be the hero - he sent Keller the wrong way to book Boro a semi-final against Arsenal.
MINUTE BY MINUTE
1min: GOAL. Dream start as Anderton pounced on Cooper slip from Carr's cross, finish from close range. 1-0.
7mins: Anderton into Kanoute, sharp turn and shot blocked by Southgate.
9mins: Keane quick feet in box, won a yard, shot into side netting from tight angle.
12mins: Anderton hooked in cross from tight angle, Southgate did enough to take sting out of Kanoute's header.
13mins: Konchesky cross flashed across goal.
17mins: Boro's first effort, Maccarone volley always going over.
19mins: SAVE. Schwarzer reactions to flick over King's header from Anderton corner.
21mins: Taricco drive from distance a yard wide.
26mins: Anderton pass released Keane on break, squared to Ricketts, shot wide from 20 yards.
45mins: MISS. Ricketts around Keller, missed target, should have scored.
Injury time: Keane on break again, forced Schwarzer to parry.
Half-time: Spurs 1-0 Boro 0
Half-time: SUB. Doherty for Richards; Downing for Maccarone.
49mins: Ricketts decent headed chance but couldn't get enough power.
53mins: Kanoute break, attempted cross deflected away from Keane.
61mins: Kanoute couldn't quite get enough on Keane cutback.
63mins: Doherty brilliant block to deny Juninho.
66mins: Zenden vicious free-kick through crowded box straight into Keller's hands.
77mins: SUB. Poyet for Anderton.
79mins: Right-foot screamer from Konchesky sailed wide.
80mins: SUB. Nemeth for Cooper.
81mins: SAVE. Keller big save to deny Juninho after lucky break saw ball land at his feet.
82mins: YELLOW. Mills for foul on Keane.
85mins: GOAL. Ricketts luck of the bounce from Boateng cross, tucked away. All started from our throw deep in Boro's half. 1-1.
Injury time: Gardner toe-end deflected Nemeth's shot wide.
Injury time: SAVE. Save of season from Keller to palm over Ricketts' point-blank header.
Full-time: Spurs 1-1 Boro
Extra-time, 1st half
95mins: Spectacular overhead kick from Poyet just over.
95mins: SUB. Dalmat for Ricketts.
98mins: CLOSE. Downing volley back across goal from tight angle inches wide.
Extra-time, 2nd half
106mins: Poyet chance after good work from Dalmat but scooped shot over from 18 yards.
108mins: King flashed 25 yarder just wide.
114mins: Ricketts header inches wide - he thought he'd scored!
116mins: Juninho good chance, 10 yards out, but failed to hit target.
119mins: Ricketts and Juninho somehow missed Nemeth cross.
120mins: SAVE. Amazing save from Keller to tip aside Downing's piledriver.
Full-time, extra-time: Spurs 1-1 Boro
PENALTY SHOOT OUT
Keane: SCORED. 1-0.
Ricketts: SCORED. 1-1.
Carr: SCORED. 2-1.
Juninho: SCORED. 2-2.
Konchesky: SCORED. 3-2.
Zenden: SCORED. 3-3.
Poyet: SAVED. 3-3.
Mills: SCORED. 3-4.
Kanoute: SCORED: 4-4.
Mendieta: SAVED. 4-4.
Taricco: HIT POST. 4-4.
Queudrue: SCORED. 4-5.
BORO WON 5-4 ON PENALTIES.
Line-ups: Spurs: Keller, Carr, Taricco, Richards (Doherty, 45), Gardner, King, Ricketts (Dalmat, 95), Anderton (Poyet, 77), Konchesky, Keane, Kanoute. Subs: Burch, Postiga.
Middlesbrough: Schwarzer, Mills, Boateng, Juninho, Cooper (Nemeth, 80) Southgate, Mendieta, Zenden, Ricketts, Maccarone (Downing, 45) Queudrue. Subs: Jones, Davies, Riggott.
Referee: Mike Dean