Paterson's persistence then caused confusion in the Tottenham penalty area, but keeper Heurelho Gomes cleared the danger.
After holding off the attention of Tom Huddlestone, he slotted home superbly past Heurelho Gomes from an angle.
The Dutchman then missed a retaken second spot-kick, before the Trotters hit back when Daniel Sturridge's shot squirmed under Heurelho Gomes.
Incredibly Bent also saw two penalties saved by Spurs keeper Heurelho Gomes.
But Bolton played their part, Heurelho Gomes twice saving from Matthew Taylor.
Tottenham boss Harry Redknapp called for match officials to use technology which might have overturned Webb's decision that Heurelho Gomes had fouled Michael Carrick.
Goalkeeper Heurelho Gomes saved from Zlatan Ibrahimovic and Pato, while William Gallas kept Milan at bay with a priceless goal-line clearance from Robinho's deflected shot.
Earlier, Jamie O'Hara and Didier Zokora dragged shots wide for Spurs, while Emile Heskey was denied by Heurelho Gomes and Amr Zaki headed just wide.
He showed the brilliant technique that has illuminated the Premier League with a bending 30-yard set-piece that left Spurs keeper Heurelho Gomes rooted to the spot.
Former Spurs winger Simon Davies was credited with the first goal, though it was another awful error by Heurelho Gomes, who fumbled into his own net.
He came closest when he ran on to Joe Cole's dummy and produced an exquisite chip which the backtracking keeper Heurelho Gomes fantastically tipped over the bar.
William Gallas is good, although you might prefer Ledley King or Michael Dawson alongside him, while I am still not 100% sold on the keeper Heurelho Gomes.
Preston, who lost at home for the first time since April, certainly had opportunities to score but were all too often thwarted by in-form Spurs goalkeeper Heurelho Gomes.
The turning point came in the second half as Darren Bent won a penalty after being pulled down by home keeper Heurelho Gomes, who appeared lucky to escape a red card.
Michael Dawson lost his footing as he went to make a clearance and Frederic Piquionne pounced to beat Heurelho Gomes from eight yards and lay the foundations for Pompey's unlikely progress.
Also omitted from the Spurs squad submitted to the Premier League today was goalkeeper Ben Alnwick, with new loan signing Stipe Pletikosa now providing back-up to Heurelho Gomes and Carlo Cudicini.
Arsenal took up the challenge and Van Persie was twice a threat in the immediate aftermath of Bentley's goal, forcing Heurelho Gomes into a save low down and then shooting just wide.
Goalkeeper Heurelho Gomes, whose performances have been called into question since his summer move from PSV Eindhoven, again looked shaky as Bolton put plenty of crosses into the box to test the Brazilian.
Twente striker Bryan Ruiz robbed Sebastien Bassong of possession and, after racing clean though on goal, tried to chip a shot over keeper Heurelho Gomes, who stuck out a vital hand to excellently save.
The result was a sudden injection of urgency, with Riga - clearly intent on making the most of a rare chance to impress - offering Heurelho Gomes his first real tests of the night.
Marc Albrighton's cross drifted beyond Spurs goalkeeper Heurelho Gomes with eight minutes left to set up the prospect of a grandstand finish, but for all Villa's effort they could not snatch an unlikely equaliser.
Long-range efforts from Carlos Tevez and Robinho - the first flashed wide, the second tipped over by Heurelho Gomes - were all the visitors had to show for their monopolisation of the football in the first half.
Wayne Rooney remains out of sorts but also produced two of United's real moments of danger when he wasted an early chance and forced a fine save from Spurs keeper Heurelho Gomes early in the second half.
The Holland international gave Liverpool the lead in the sixth minute with a low shot from the edge of the area which flew past Heurelho Gomes' right-hand after he had been set up by Italian playmaker Alberto Aquilani.
It might have been different for Portsmouth, though, had Vanden Borre made the most of the first real chance of the game when he found himself clear in the box only for keeper Heurelho Gomes to save his tame effort.
The summer signing of Brazilian goalkeeper Heurelho Gomes from PSV Eindhoven gave a strong indication that Robinson was not going to figure uner manager Juande Ramos -- and he has chosen to return north after starting his career with Leeds United.
Spurs goalkeeper Heurelho Gomes denied Hassan Yebda with a superb late save before home midfielder Michael Brown was sent off for two bookings in time added on against his former club, as manager Harry Redknapp enjoyed a triumphant return to Fratton Park.
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