A bright start to the game disappeared as between 23 and 28 minutes Boro took the lead against the run of play, Chris Perry was controversially sent off after a challenge with Szilard Nemeth and Juninho doubled the lead from the spot before Nemeth struck from close range.
Incredibly, this all came against the run of play after we'd dominated the early stages and kept the ball for fun for minutes on end.
Indeed, Boro had lost influential defender Ugo Ehiogu through injury the home crowd were getting restless - the signs were good.
Our possession finally created two chances in two minutes as Teddy Sheringham volleyed Mauricio Taricco's cross inches wide after 18 minutes and then found himself in the clear, 10 yards out, only to slip after turning Riggott inside out and shoot into the side netting.
But it went downhill pretty fast midway through the half.
Boro opened the scoring after 23 minutes as Nemeth turned inside Perry, Keller saved his shot only for the rebound to fall to Malcolm Christie, who made no mistake from close range.
It went from bad to worse than worse a minute later. Nemeth burst onto a pass through the middle pursued by Perry. Nemeth appeared to lose control of the ball, the pair came together and without hesitation, referee Uriah Rennie awarded a penalty and sent Perry off. To add insult to the red card, Keller 'saved' Juninho's spot kick only for the ball to spin across the line where the Brazilian tapped home.
Keller tipped Juninho's shot wide but it was soon 3-0 and more ill fortune - Wilkshire's shot hit King and fell kindly to Nemeth, who tucked the ball into the bottom corner.
In the space of five minutes we'd gone from being in control to 3-0 down with 10-men - shellshocked doesn't do it justice.
Once we regained some composure, we carved out another couple of chances as Mark Schwarzer tipped Steve Carr's free-kick over and was soon out bravely to deny Sheringham.
There was always a threat at the other end though with the pacy Juninho, Christie and Nemeth around and both Keller and Anthony Gardner did well to cut out potential danger.
Half-time brought changes as Matt Etherington and Jamie Redknapp - a return after five months out of Premiership action - replaced Sheringham and Gus Poyet. Massimo Maccarone also came on for Christie.
There was little respite however and it took Boro five minutes to add the fourth goal when Nemeth slid in to nick the ball away from Ledley King, played in Maccarone and the Italian made no mistake one-on-one.
Wilkshire was denied by Keller and Greening shot over before a magnificent response from Redknapp, a 30-yard free-kick into the top corner and unqueastionably the goal of the game.
Inevitably it was one-way traffic though and Boro hit the woodwork twice through Nemeth and Wilkshire before Maccarone added the fifth from Juninho's pass.
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3mins: Good work from Juninho to create a chance but screwed shot well wide.
10mins: SUB. Riggott for injured Ehiogu.
18mins: CLOSE. Having kept possession for fun for most of the game so far, first chance created as Taricco's low cross volleyed inches wide by Sheringham.
20mins: CHANCE. Another fine move, one-two between Gardner and Keane, low cross, Sheringham spun away from Riggott, clear, 10 yards out, but appeared to slip as he shot into side netting.
22mins: CLOSE. Juninho free-kick from 25 yards had Keller scrambling but landed a foot wide.
23mins: GOAL. Nemeth onto Wilkshire's pass, turned inside Perry, Keller saved initial effort but Christie slammed home rebound. 0-1.
24mins: RED CARD/PENALTY/GOAL. Looked a poor decision. Nemeth raced through pursued by Perry, Nemeth lost control and fell over his own feet but Uriah Rennie awarded a penalty and sent Perry off! To add to it all, Keller saved Juninho's penalty but the ball spun away from him and Juninho tapped home on the line. 0-2.
27mins: SAVE. Keller just managed to tip Juninho's shot wide.
28mins: GOAL. More bad luck. Shot from the edge of the area was blocked but fell kindly to Nemeth just 10 yards out and he tucked it into the bottom corner. 0-3.
34mins: SAVE. Carr's free-kick tipped over by Schwarzer.
35mins: Lightning Boro break from our corner, five on three, but Christie's attemped cutback read and collected by Keller.
38mins: SAVE. Keane weaved his way past three men and played one-two with Sheringham, fine tackle from Queudrue but ball fell to Sheringham, whose close-range effort was blocked bravely by Schwarzer.
40mins: Great last-ditch tackle from Gardner as Wilkshire pulled the trigger 12 yards out.
Injury time: YELLOWS. Bunjevcevic booked ridiculously when a Boro player kicked the ball against him in pretending to take a quick free-kick. Poyet booked for altercation with Boateng.
Half-time: Boro 3-0 Spurs
Half-time: SUBS. Etherington and Redknapp for Sheringham and Poyet; Maccarone for Christie.
50mins: GOAL. Nemeth slid in and nicked the ball away from King and played in Maccarone, who made no mistake one-on-one. 0-4.
54mins: SAVE. Keller at full stretch to divert Wilkshire's free-kick.
57mins: Decent move ended with Greening's shot just over from 18 yards.
60mins: GOAL. Delightful free-kick into the top corner from Redknapp. 1-4.
61mins: CHANCE. Maccarone should have done better from 15 yards but shot wide.
64mins: Davies couldn't quite get onto Redknapp's clever pass.
67mins: WOODWORK. Juninho away from Davies and Gardner, square pass played in Nemeth who hit the foot of the post from 12 yards.
69mins: Great crossfield pass from Nemeth found Juninho, low shot, Keller up to the task.
70mins: MISS. Wilkshire completely clear 15 yards out, blazed over.
71mins: DOUBLE WOODWORK. Wilkshire shot hit both posts before bouncing wide off Keller.
75mins: GOAL. Juninho into Maccarone, slid ball under Keller from 10 yards. 1-5.
77mins: SUB. Downing for Wilkshire.
86mins: MISS. Maccarone played through Boateng, lifted the ball over Keller but over the bar as well.
87mins: Queudrue's free-kick deflected just wide by the defensive wall.
89mins: MISS. Maccarone's pace took him beyond Gardner only to poke chance wide.
Line-ups: Middlesbrough: Schwarzer, Stockdale, Queudrue, Ehiogu (Riggott, 10), Southgate, Boateng, Nemeth, Juninho, Greening, Christie (Maccarone, 45), Wilkshire (Downing, 77). Subs: Jones, Doriva.
Spurs: Keller, Carr, Taricco, Perry, Gardner, King, Poyet (Redknapp, 45), Bunjevcevic, Davies, Sheringham (Etherington, 45), Keane. Subs: Acimovic, Yeates, Burch.
Five minutes of madness paved the way for a miserable afternoon at the Riverside.