The match finished level at full-time thanks to Wayne Rooney's late leveller, but Chelsea's second goal had sparked controversy.
Chelsea substitute Michael Ballack appeared to elbow Patrice Evra, but while the French left-back lay hurt on the ground referee Chris Foy allowed play to continue.
Chelsea's Didier Drogba broke clear of the United defence before slipping the ball to Frank Lampard to fire the Blues ahead.
Evra then had to be kept apart from Ballack and was booked for a cynical foul on the Germany captain in the 80th minute.
But with Chelsea heading for victory, Rooney broke clear to level the scores in the final minute and take the game to penalties.
Cech then saved from substitute Ryan Giggs and the luckless Evra, to earn Chelsea a 4-1 victory on spot-kicks.
In contrast to the ill-feeling in the later stages of the contest, the afternoon had begun in a more fitting fashion with one minute's applause for the late Sir Bobby Robson.
When the action began on the pitch, United goalkeeper Ben Foster was tested within the opening two minutes.
Drogba collected a pass from Lampard and fired a 20-yard shot towards goal but Foster, selected in the England squad for Wednesday's friendly against Holland, saved at the second attempt.
It was a bright start by Chelsea who almost went ahead in the fifth minute.
Lampard's corner was met by right-back Branislav Ivanovic whose effort was headed against the bar by Evra.
United took the lead with their first real attack of the game in the 10th minute.
Darren Fletcher's sublime cross-field pass was collected by Nani and the Portugal winger beat Ivanovic and Michael Essien before sending a 25-yard drive beyond Cech and into the far right corner.
United should have made it 2-0 in the 16th minute when Dimitar Berbatov crossed for Rooney to head the ball back to Park Ji-Sung on the edge of the six-yard box.
Park was thwarted by a great save from Cech, and the Chelsea goalkeeper then pulled off another fine save moments later when the South Korean midfielder set Berbatov through on goal.
Chelsea were beginning to exert some control as the interval approached but they failed to find a cutting edge.
That lack of precision was underlined again five minutes before the break when Nicolas Anelka sent a drive just wide of Foster's left-hand post.
A cross from Ivanovic moments later failed to trouble Foster even through Drogba lurked with intent.
Three minutes before the break Cech had to be at his best again to tip a 20-yard shot from Fletcher over the bar.
Chelsea replaced the struggling Ivanovic with Jose Bosingwa at the start of the second half, and equalised in the 52nd minute through Ricardo Carvalho's diving header.
Lampard and Florent Malouda had combined on the left and when the winger sent over a volleyed cross, Drogba and Foster collided as they went for the ball.
Foster's attempted clearance fell straight to Carvalho who dived to head the Blues level from eight yards.
Chelsea were full of confidence and Anelka soon tested Foster with a powerful 20-yard drive that the United goalkeeper did well to push away to safety.
In the 59th minute Drogba was inches away from meeting a cross from Ashley Cole as Ancelotti's side continued to control the game.
United were rocked by an injury to goalscorer Nani on the hour. The winger hurt his shoulder in a clash with John Terry and was replaced by Antonio Valencia.
Three minutes later Chelsea replaced John Mikel Obi with Germany captain Ballack.
The London outfit took the lead in controversial circumstances in the 70th minute after Ballack appeared to elbow Evra.
While the United player was down Chelsea broke away and Drogba's pass to Lampard allowed the England midfielder space to beat Foster with a crisp drive. The ball struck the inside of the left post and bounced over the line before spinning back out, however it was clearly a legitimate goal.
With seconds remaining Rooney broke clear of the Chelsea defence and slipped the ball beyond Cech for a dramatic equaliser, but United were not so clinical in the shoot-out.
Source: ESPN Soccernet, August 9, 2009
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