Nicolas Anelka's early strike inflicted a second Barclays Premier League defeat of the season for United, who turned in an uncharacteristically subdued performance at the Reebok Stadium.
Gary Megson's struggling Trotters side battled ferociously for the victory, but were aided by a Reds performance which only got going in the final 20 minutes, when an incredible miss from Carlos Tevez ultimately proved costly.
The Argentine striker somehow contrived to stab the ball wide from inside the six-yard box after a fine cross from Patrice Evra, spurning easily the best chance of a frustrating afternoon for United.
Cristiano Ronaldo was omitted from the Reds squad entirely, having posted two full matches for Portugal during last week’s international break. Nemanja Vidic, meanwhile, failed to recover from a back injury sustained on duty with Serbia, and he was replaced in the starting line-up by Gerard Pique.
The young Spaniard, making his second Premier League start for the Reds, was caught out as Bolton took the lead after 11 minutes. Pique tried to head Ivan Campo’s clipped free-kick clear but misjudged the flight of the ball, allowing Anelka to control, turn and sweep a finish past Edwin van der Sar.
Clearly invigorated by the recent appointment of manager Gary Megson, Bolton were living up to the snarling, energetic reputation built up during Sam Allardyce’s time at the Reebok helm. United, in stark contrast, looked totally out of character for the majority of the first half.
But for wayward shots from Louis Saha and Owen Hargreaves, United had little to show for their possession. Patrice Evra had bumps and bruises from the opening half, however, thanks to a running battle with robust Trotters striker Kevin Davies, who was booked for a late lunge on the French international defender.The interval came and went with little action either side of it, although Sir Alex Ferguson was sent to the stands for remonstrating with the officials at the end of the first period. The hosts rarely threatened in an attacking sense, but the absence of United's trademark slick passing and ball retention made for a desperately poor game.
With half an hour remaining, Sir Alex replaced Pique with Brazilian midfielder Anderson, switching Wes Brown to the centre of defence and Owen Hargreaves to right-back.
It was the makeshift full-back who had United's first on-target effort of the match almost immediately afterwards. After Evra had been brought down 25 yards from goal, Jussi Jaaskelainen had to be alert to tip Hargreaves' free-kick over the bar.
That effort prompted United's first spell of sustained pressure, with Anderson's buzzing intent right at the hub. Nani fizzed a shot past Jaaskelainen's near post, before Tevez somehow flicked Evra's cross wide with the goal gaping.
United were appealing long and loud for a penalty with 10 minutes remaining, as Nani saw his cross ricochet off Ricardo Gardner's upper arm inside the area, but referee Mark Clattenburg waved away the claims.
As the game entered stoppage time Evra burst onto Giggs' through-ball but, rather than slide the ball back for the unmarked Saha, the full-back slashed a shot high over the bar.
There was still time for just one more chance, but Hargreaves' 25-yard free-kick agonisingly cleared the bar and clipped the roof of the net.
The frustration perfectly summed up a painful afternoon for United, who were left to rue an under-par performance and a second league defeat of the season.
Bolton Wanderers: Jaaskelainen; Hunt, Meite, A O'Brien, Gardner; Guthrie (Wilhelmsson, 74), Nolan (McCann, 82), Campo, Diouf; Davies (Speed, 70), Anelka.
Subs not used: Al-Habsi, Michalik.
Manchester United: Van der Sar; Brown (O'Shea, 89), Ferdinand, Pique (Anderson, 59), Evra; Nani, Hargreaves, Carrick, Giggs; Tevez, Saha.
Subs not used: Kuszczak, Fletcher, Eagles.
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