Drogba’s precise free-kick just before the hour mark was the decisive moment of an incident-packed FA Cup final in which Chelsea hit the woodwork five times in the first half and both sides also missed from the penalty spot.
Chelsea – who become only the seventh club to win the coveted domestic Double – were again grateful to the prolific Drogba, who kept up his remarkable record of scoring in each of his six games at Wembley with his 37th goal of the season.
He scored only minutes after Pompey’s Kevin-Prince Boateng saw his half-hit penalty saved by Chelsea keeper Petr Cech – and in that moment Pompey’s chances of repeating their victory of two years ago effectively disappeared.
Chelsea were even able to survive a rare penalty miss by Frank Lampard in the closing minutes when he shot wide from the spot after he had been brought down by Michael Brown.
The margin of victory belied Chelsea’s superiority, especially in a remarkable first half when Lampard, John Terry, Salomon Kalou and Drogba, on two occasions, all struck the frame of the goal.
Portsmouth bravely held on but wasted their own big chances in the shape of Boateng’s penalty miss and a Frederic Piquionne effort from six yards that was scrambled away by Cech before the break.
It is a victory that caps a remarkable campaign for Ancelotti – and there was a personal honour for defender Ashley Cole, who became the most decorated player in FA Cup history by picking up his sixth winner’s medal.
Pompey battled with the resolve that has taken them to Wembley against a background of financial meltdown and relegation to the Championship under manager Avram Grant.
But Chelsea had the extra weaponry when it mattered to deprive the Fratton Park club of any consolation at the end of a troubled campaign.
And Ancelotti, the modest and dignified Italian, took another step towards banishing the ghost of Jose Mourinho from Stamford Bridge by writing a new chapter in the club’s record books.
Lampard was first to feel the woodwork frustration when, after shooting inches wide, he glanced the outside of the post with a swerving effort from 20 yards that left James helpless.
Pompey had performed with great heart throughout a Cup run that had salvaged something from the wreckage of their season and they should have gone ahead after 21 minutes.
Boateng volleyed Aruna Dindane’s cross into the six-yard area and Piqiuonne’s instinctive finish was met with equally sharp reflexes from Cech, who clawed away the ball.
The rest of the opening period was a tale of sustained Chelsea pressure, with Pompey hanging on via a mixture of brave defence and outrageous good fortune.
Kalou was guilty of a dreadful miss after 26 minutes, hitting the bar from almost on the line after Cole delivered a cross that seemed impossible to miss.
Chelsea captain Terry rose in towering fashion to head Florent Malouda’s free-kick against the bar before Drogba then thought he had finally given Chelsea the lead.
The Ivorian’s 30-yard free-kick took Portsmouth by surprise but James – the oldest goalkeeper to play in an FA Cup final at 39 years and 287 days – reacted to turn it on to the bar and down on to the goalline. The officials remained unmoved as Chelsea appealed for a goal but replays showed the ball did not fully cross the line.
There was still time for Drogba to hit the post again, this time from an acute angle, as Portsmouth somehow remained on terms at the interval.
And their spirits soared after 54 minutes when Juliano Belletti, on as a first-half substitute for Michael Ballack, who suffered an ankle injury, brought down Boateng as he raced into the area.
Referee Chris Foy had an easy decision to point to the spot – but Cech’s save was just as easy from Boateng’s woeful penalty.
And the dire consequences of the miss were emphasised five minutes later when Drogba ended the charmed life the Pompey goal had led. The positioning of keeper James may be questioned but Drogba’s placement was perfect, scoring low in the corner via the upright.
Kalou then dragged a finish wide from a good position, his final contribution as he was replaced by Joe Cole with 20 minutes left. Cole received a huge ovation from the Chelsea fans amid growing speculation this could be his final game for the club before quitting on a free transfer.
And he almost scored with his first touch after Drogba saw his shot saved by James at the near post. Drogba then teed up Cole – but he miscued his effort and the chance was gone.
Chelsea were given the opportunity to give the scoreline a more convincing appearance when Lampard was fouled inside the area by Brown but he contributed to the seemingly endless drama by kicking wide.