Cremonese
Felix Afena-Gyan struck the winning spot-kick under a torrential downpour in Naples to send Cremonese through after the former Roma forward had taken the match to extra time with a late looping header.
Napoli had been leading 2-1 with three minutes remaining of normal time thanks to headers in three first-half minutes from Juan Jesus and Giovanni Simeone after Charles Pickel gave the away side an 18th-minute lead.
But Cremonese fought back against an initially second-string Napoli and Luciano Spalletti was forced to bring on star striker Victor Osimhen just after Leonardo Sernicola was sent off in a bid to win the tie.
The Nigeria forward drew a superb save from Marco Carnesecchi late in the first half of extra time before Simeone smashed his rebound effort off the post and bar with an open goal at his mercy.
But Cremonese, under new coach Davide Ballardini after Massimiliano Alvini was sacked on Sunday with the team winless after 18 league matches, held off a Napoli onslaught in soaking conditions and held their nerve in the shootout.
Ballardini's team netted all five of their spot-kicks while Stanislav Lobotka missed his for Napoli, who exit the competition early.
Tuesday's match was also the first time an all-female on-pitch team of officials took charge of a match featuring two Serie A clubs.
Referee Maria Sole Ferrieri Caputi, who was promoted to the top rung of Italian football's match officials in the summer, was flanked by assistants Francesca Di Monte and Tiziana Trasciatti.
Ferrieri Caputi made history in October as the first woman to referee a Serie A match when she officiated Sassuolo's 5-0 thumping of Salernitana.
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