This was considered a match that Hammers simply could not afford to lose, a billing that would hopefully bring out the best in Glenn Roeder's team and inspire them to produce the kind of winning performance that most of us know they are capable of but haven't provided often enough this season.
Sadly, such a display didn't materialise and the 3,500 travelling Hammers fans were left to reflect on another hugely disappointing afternoon that brought plenty of enthusiasm and endeavour, but simply not enough quality to turn possession into goals when it mattered most.
Bolton, however, had the talents of Okocha to call upon. The Nigerian international hit a post before firing home the winner in stunning fashion just seven minutes before the break, and was a constant thorn in Hammers' side as he cleverly used the acres of space in between our midfield and defence.
Prior to the game, Roeder had been forced to make one change to the team that drew 2-2 with Aston Villa last weekend, as Lee Bowyer missed out through injury. His place was taken by Edouard Cisse, with Michael Carrick still not recovered from a troublesome groin injury.
Bolton had the first effort of the game in the third minute, as Okocha fired a volley high over the bar from the edge of the penalty area after a corner had been headed out. Just moments later, though, Hammers created an even better opening, as Defoe's neat lay-off released Kanoute who, with just one man to beat, decided to attempt a chip, but sadly his effort didn't even get off the ground.
The chance certainly lifted the visitors, though, and Defoe came close himself in the seventh minute, robbing Charlton on the right and skipping into the area before firing in a cross-shot that Jaaskelainen held comfortably.
Thanks to Okocka, though, Bolton retained their danger, and the Nigerian almost opened the scoring in the 13th minute with a thunderous right foot drive from 25 yards out that cannoned off James' near post and away to safety.
Kanoute then fired a low shot just wide of the upright and, as the halfway mark in the first half approached, there was nothing to spare between the two sides.
The turning point arrived in the 38th minute. Following another breakaway attack, Defoe saw a shot blocked after he beat the offside trap on the right and cut inside on to his left foot. The loose ball rebounded to Cisse, whose shot from 25 yards out was also blocked and, from the resulting clearance, Okocha picked up the loose ball and shrugged off the challenge of Cole in midfield before advancing forward.
As Hammers' central defensive pairing of Tomas Repka and Ian Pearce backed off - a sadly familiar sight all afternoon - Okocha carried on running, before unleashing a stunning 20-yarder that rocketed into the top corner beyond the despairing dive of James.
Two minutes later, the Nigerian almost doubled his tally as he latched on to a pass from Pedersen, but this time James came to the rescue with a brave dive to smother the ball at his feet. N'Gotty's powerful effort was then tipped over by the Hammers keeper, and the half-time whistle couldn't come soon enough for Roeder's men.
Hammers started the second half in determined fashion, although there was an early scare when Glen Johnson reacted to a challenge from Djorkaeff and wrestled the Frenchman to the ground in front of the baying home fans. Thankfully, referee Uriah Rennie saw that the youngster had shown no malice and brandished just a yellow card.
Bolton's Mendy was then booked himself for a late challenge on Cole and, after a fairly tepid first 45 minutes, the game at last appeared to be shaping into the full-bloodied relegation battle that both sets of fans had a right to demand.
Cole - trying his hardest to stir his team-mates and launch a comeback - set off on a mazy run in the 61st minute that saw him beat three players, but the captain dragged his left-foot shot well wide of the target. Defoe then appeared to have broken free in the box, only to be pulled back by N'Gotty as he chased after the loose ball. However, Rennie waved away the appeals for a penalty, much to the dismay of the young striker.
In the 65th minute, Roeder introduced Les Ferdinand from the substitutes' bench. He replaced Cisse as the Hammers boss gambled on a three-pronged attack in a bid to put the hosts under more pressure. The arrival of the veteran striker gave Hammers a much-needed lift and his presence helped create a glorious chance in the 68th minute, the ball running loose to an unmarked Kanoute, who looked set to score but touched the ball too far ahead of himself and allowed a defender to make a saving tackle.
Defoe was then harshly booked for a tussle with Laville that seemed to more the doing of the French defender and things went from bad to worse for the 20-year-old in the 75th minute when he fired wide from just 10 yards out after being put in the clear.
As expected, Hammers had the majority of the play in the closing stages, but the blustery conditions and a resolute Bolton defence contributed to the lack of creativity and, disappointingly, there wasn't a single effort on target from the visitors in the final 10 minutes.
To compound Hammers' misery, Ian Pearce was shown a red card after his desperate late challenge on substitute Andres and subsequent shove on Nolan. The incident sparked a mass brawl that continued after the final whistle when Cole angrily confronted Rennie - who strangely didn't punish any Bolton player during the melee - and then became involved in an altercation with Mendy, who appeared to aim a headbutt at the Hammers captain before he was ushered down the tunnel by his team-mates.
Unfortunately, Cole may now be punished for allowing his frustrations to boil over. Once again, the 21-year-old had led by example throughout and was clearly hurt and upset by a defeat that could prove more costly to the future of West Ham United than we dare imagine.