With just four minutes to go referee Peter Walton had dismissed the Wanderers goalkeeper Jussi Jaaskelainen after he was adjudged to have brought down Boro striker Jimmy Floyd Hasselbaink who was through on goal.
Walton then added on a large amount of injury time which subsequently lead to Boro snatching an equaliser through George Boateng after substitute goalkeeper Kevin Poole had parried an initial shot from Ray Parlour.
The first half had been very much a question of possessional play with neither side able to make the breakthrough in the final third of the field. The second half in contrast showed much improvement from both teams as they looked to improve on their lofty positions.
Bolton striker El-Hadji Diouf was at constant loggerheads with his marker Parlour throughout the afternoon and this was to make the Senegalese striker a target for the home crowd who were far from happy with some of his antics.
At times Diouf had a case to argue, but it was clear to see that the former Arsenal man Parlour knew exactly how to push the destruct buttons of the African attacker.
On the half hour mark in the first period the Wanderers had a shout for a penalty waved away after midfielder Kevin Nolan had gone to ground following a challenge from behind by his Boro counterpart Boateng.
Eight minutes later the Trotters man of the moment Radhi Jaidi saw a stinging volley deflect off his own player Stelios Giannakopoulos following good work from Kevin Davies and Bruno N'Gotty.
Carling Cup Final hero Bolo Zenden had Boro's best effort of the half but this was to go high wide and handsome over Jussi Jaaskelainen's crossbar. In truth it was a relief for both sides to go in for the half time teamtalk after a patient, yet lifeless, first period.
After the interval the home side introduced bustling striker Mark Viduka in place of the ineffective Joseph Desire Job. The Australian almost made an immediate impact when heading Stewart Downing's left wing cross onto the post.
On 50 minutes Bolton striker Diouf had the perfect opportunity to silence the jeers from the home crowd but his shot on the turn following a ball from Kevin Davies was comfortable enough for the Middlesbrough keeper Mark Schwarzer.
Ten minutes later it was the turn of Spaniard Fernando Hierro to try and work the Boro goalkeeper. Unfortunately for the Spaniard he was to fire high and wide over the crossbar.
Soon after that attempt, team mate Ricardo Gardner also hit his effort into the stands despite an excellent mazy run down the left which saw him beat a number of Middlesbrough defenders.
Boro striker Viduka had another chance to open the scoring on 66 minutes following a further cross from the left. This time the ex-Leeds and Celtic striker hit the side netting.
Bolton then brought their top goalscorer Henrik Pedersen into the fray in an attempt to change things for the better. This proved to be an inspired substitution for the Wanderers as the Danish striker put them ahead on 72 minutes. A left wing corner from Diouf was headed goalwards by French defender Bruno N'Gotty and Pedersen was the quickest to react when steering the ball past Schwarzer.
With 15 minutes remaining Bolton's Kevin Nolan conceded a free kick after shoving Hasselbaink on the edge of the box. The Boro striker had beaten the Wanderers goalkeeper Jaaskelainen but the post once again came to the rescue of Sam Allardyce's team.
The closing stages saw the later drama unfold, a long punt upfield by Boro goalkeeper Schwarzer saw Hasselbaink in a one on one position with Bolton stopper Jaaskelainen. The Finn appeared to tangle with the ex-Chelsea forward just outside the area leaving referee Walton no option but to show the player a red card.
Wanderers veteran goalkeeper Kevin Poole then entered proceedings for his 300th career game against one of his former clubs but the 41-year old could do little to stop Boateng's equaliser despite parrying the initial shot from Parlour.
Not a good day at the office as far as Wanderers are concerned. Boro will feel they had secured a deserved point but the Trotters will be unhappy at the manner in which another Premiership win slipped from their grasp.