Bosingwa played alongside his new Chelsea team-mates Ricardo Carvalho and Paulo Ferreira at Porto.
And it reaped a reward after only three minutes when the makeshift central defensive partnership of Paulo Ferreira and Michael Essien was ruthlessly exposed.
Hilario failed to deal with a deflected Brett Emerton cross and Benni McCarthy scored a penalty, but Paulo Ferreira levelled at 3-3 deep into extra-time.
El-Hadji Diouf equalized for the home side in the 70th minute when he rose above Paulo Ferreira to cleverly direct Michel Salgado's cross past Petr Cech.
And there was no escape from rampant Barcelona with 10 minutes remaining, with Rafael Marquez's cross finding Eto'o, who rose above Paulo Ferreira at the far post to seal the win.
Terry and Alex were missing, so into their places in the centre came Branislav Ivanovic and Paulo Ferreira, who is a right-back by trade and not the most solid defensively anyway.
The return of Alex at centre-half seemed to do the trick in restoring confidence to the Chelsea ranks, while Paulo Ferreira's switch to right-back and Salomon Kalou's recall certainly helped the balance.
It looked as though the home team would seal victory in extra-time after Benni McCarthy had scored a penalty to make it 3-2, but Paulo Ferreira struck deep into injury-time to take the match to penalties.
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The first effort on target did not arrive until after the half-hour, with Paulo Ferreira venturing forward and slipping a pass in for Frank Lampard, who forced Van der Sar to make a smart low save.
Chelsea had the ball in the net eight minutes before halftime, but Florent Malouda was clearly offside, and then Bale made it 2-0 soon after as he cut inside Paulo Ferreira and whipped a low right-foot shot past goalkeeper Petr Cech.
But unlike in the Carling Cup final, this time Villa did not get a penalty when the striker was brought down by Jon Mikel Obi, who was in all likelihood the last man as it seemed Paulo Ferreira was unlikely to get across and cover.
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The data was released just hours after Sao Paulo's security chief, Antonio Ferreira Pinto, resigned amid a wave of violence in the city.
However, Sao Paulo's public security secretary, Antonio Ferreira Pinto, has suggested that other criminals may be exploiting the situation to carry out attacks and let the police take the blame.
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