The first half was largely forgettable but the game came to life after the break.
El Hadji Diouf fired Bolton ahead from the penalty spot three minutes into the second half although there was some confusion at the time as to what the spot kick was awarded for - the theory in the press box was handball against either Erik Edman or Stephen Kelly and so it proved with the Swede later identified as the guilty party.
Jermain Defoe entered the fray after 65 minutes and levelled three minutes later only for Fredi Kanoute to pick up a second yellow card and sent off just 60 seconds later.
That was the turning point and put us back on the back foot although few chances were created until the home side scored in the 87th and 88th minutes with Tel Ben Haim and Kevin Davies securing Sam Allardyce's men the points.
We started with just one change from the FA Cup draw at West Brom with Robbie Keane up front in place of Defoe. New arrivals Mido and Radek Cerny were on the bench.
We stood up well to the aerial bombardment in what was, in truth, a poor first half.
Bolton hit ball after ball into the box but Paul Robinson, Ledley King and Anthony Gardner - who picked up a nasty cut for his troubles - held firm.
Just as important, we got the blocks in to the loose balls in and around the egde of the area.
In the end Robinson fielded a number of headers notably from Davies and Bruno N'Gotty, none powerful enough to threaten, and one tricky volley from Kevin Nolan that bounced awkwardly just in front of him.
At the other end, Kanoute arguably had the best chances of the half, drilling just wide from 22 yards after five minutes and glancing Michael Carrick's corner over having beaten Jussi Jaaskelainen in the air.
The second half was a different story. Diouf made no mistake from 12 yards three minutes in after Mike Dean spotted an infringement and Kanoute was then booked for his protests as he appealed for a penalty after his free-kick struck Bolton's defensive wall.
Jaaskelainen then kept us at bay with the two best saves of the night to deny Brown from 25 yards and Stephen Kelly from close range.
Defoe was soon into the action and made a typical, instant impact. Robinson's throw released Keane, he ran 30 yards down the left side before picking out Defoe on the edge of the box, the striker hit the ball low and hard but Jaaskelainen might have done better.
Nevertheless, it was 1-1 and suddenly we were hoping to go on and take the victory.
However, the wind was very quickly taken out of our sails when Kanoute was handed a second yellow for a foul on Barness and our hopes of winning trudged off with him, 21 minutes left.
Still, few chances were created and a draw looked on until the final three minutes.
It started when Gardner toed the ball just wide as Robinson came to claim Ricardo Gardner's cross and from the corner, Tel Ben Haim rose high to power home his header from 12 yards.
Seconds later and it was all over. We were all out for an equaliser, Bolton broke away, Diouf crossed for Davies and that was that.
GUIDE TO THE ACTION
4mins: Keane did well to muscle out N'Gotty, drove ball across goal, no support.
5mins: CHANCE. Kanoute worked a yard on the edge of the box, shooting chance, drilled it a yard wide.
7mins: Bolton's first effort, Campo free-kick from right, N'Gotty's looping header, no danger for Robinson.
8mins: Another free-kick, this time taken by Hunt, half-cleared, Barness volley looked on target but blocked by Edman.
11mins: MISS. Kanoute managed to get in front of Jaaskelainen to meet Carrick inswinging corner but glanced header over from six yards.
18mins: Davies cross taken well by Kanoute who controlled, spun and volleyed just over from 20 yards.
22mins: Good move from Bolton, Nolan inside to Speed, 18 yards out, crucial tackle from Carrick as he pulled the trigger forced him to drag wide.
24mins: Nolan chested down long clearance, hit bouncing ball on volley, dipped and hit deck just in front of Robinson who was always in control.
27mins: Great charge down from Brown as Gardner let fly from 22 yards.
29mins: Davies looping header from Barness cross no problems for Robinson.
39mins: Davies climbed well to meet Stelios corner but couldn't keep header on target.
Injury time: Another free-kick, Robinson punch met by Campo, 25 yards out, blasted over.
Injury time: Stelios cross from left, Davies header straight at Robinson, no power.
Half-time: Bolton 0, Spurs 0
48mins: PENALTY. Melee in area following long throw, ball bouncing around, referee suddenly pointed to the spot. Not sure why. Suggestion is handball. Diouf belted penalty into top corner.
Bolton 1, Spurs 0
52mins: PENALTY? Appeals waved away after Kanoute's free-kick struck defensive wall.
52mins: YELLOW. Kanoute booked for protests.
56mins: SAVE. Our best move of game, Carrick to King joining in play, his run attracted couple of defenders, slipped to it Brown, now in space, rifled shot from 25 yards that Jaaskelainen spectacularly tipped over.
57mins: Campo rasper from 30 yards but Robinson behind it all the way.
59mins: SAVE. Brown picked out Kelly's late run, room to control and pick spot, struck well from 15 yards but Jaaskelainen up to the task and tipped wide.
65mins: SUB. Defoe for Edman. Atouba to left-back, three up front, Keane to left.
68mins: GOAL. Robinson quick throw released Keane, ran 30 yards before feeding Defoe, 20 yards out, low shot went through Jaaskelainen.
Bolton 1, Spurs 1
69mins: RED. Kanoute off for second bookable offence, foul on Barness.
75mins: King inches away from Carrick's corner.
77mins: Gardner headed Carrick's corner over from 12 yards.
78mins: CHANCE. Davies lovely flick inside to Hunt, King just about back to him as he dragged shot across goal from tight angle.
78mins: SUB. Fadiga for Barness.
83mins: CHANCE. Gardner cross from left fell at feet of Diouf, half-volleyed high and wide.
85mins: Quick break from Bolton attack, Keane released overlapping Kelly into box but got final pass wrong with Davies and Defoe in support.
87mins: CLOSE. Gardner cross from left, Robinson appeared to have it covered but Gardner poked out toe and deflected it just wide.
87mins: GOAL. From corner, Ben Haim rose well to power home from Stelios' kick.
Bolton 2, Spurs 1
88mins: GOAL. Bolton break from our attack, Atouba lost out to Fadiga who fed Diouf, right side, low cross to far post slid in by Davies.
Bolton 3, Spurs 1
Injury time: SUB. Pedersen for Davies, Hierro for Stelios.
Injury time: Defoe 25-yarder wide.
Full time: Bolton 3, Spurs 1
Spurs (4-4-2): Robinson, Kelly, Edman (Defoe, 65), King, Gardner; Davies, Brown, Carrick, Atouba; Kanoute, Keane. Subs: Cerny, Bunjevcevic, Mido, Marney.
Bolton: Jaaskelainen, Barness (Fadiga, 78), Nolan, N'Gotty, Speed, Stelios (Hierro, 90), Gardner, Davies (Pedersen, 90), Campo, Diouf, Ben Haim. Subs: Poole, Jaidi.
Two late goals left us with nothing to show for our efforts as we ended with 10 men in Tuesday night's defeat at Bolton.