Juventus were outclassed 3-0 by Barcelona, Napoli were beaten by Shakhtar Donetsk and AS Roma clung on for a 0-0 draw at home to Atletico Madrid.
According to Gazzetta dello Sport, it was the worst start by Italian clubs since the group stage was expanded to 32 teams in 1999/00, eclipsing the 2011/12 record when Inter Milan, AC Milan and Napoli managed a defeat and two draws between them.
Juventus and Napoli have been dominant on home turf recently, making their European humblings all the more worrying.
Juventus, champions for the last six seasons, have lost only two league games this year and Napoli have won their last eight Serie A outings.
Once seen as Europe's top domestic league, Serie A has fallen behind Spain's La Liga and England's Premier League as its television revenues have failed to keep up.
Although Juventus have reached the Champions League final twice in the last three seasons, no other Serie A side has gone beyond the last 16 since AC Milan in 2011-12 and it is 10 years since two Italian sides were in the last eight.
It was widely believed that the worst was over, with new investors coming in and more clubs looking to own their own stadiums.
But this week's events have suggested there is a long way to go and may raise questions about UEFA's decision to give Italy four guaranteed slots in the Champions League group stage from next season.
"I'm disappointed, there is nothing else to do but cry," said former AC Milan coach Arrigo Sacchi, now working as a television analyst, after Napoli's 2-1 defeat in Ukraine on Wednesday. "If you play in Europe like you do in Bologna, then you are destined to lose."
Napoli coach Maurizio Sarri said his team were too sluggish at the start.
"It's the third game in a row which we have approached the wrong way," he said. "In Serie A, we managed to rescue ourselves but, at this level, it was difficult to change to story after such a bad opening 20 minutes."
Napoli have a straightforward match on Sunday when they host promoted Benevento, who have lost their opening three matches.
Juventus and Roma also face winless opponents as the champions visit Sassuolo and last season's runners-up host promoted Verona.
Juventus coach Massimiliano Allegri said it was too early to jump to draw conclusions from the Barcelona match.
"It was just the first game in the group so the criticism is exaggerated," said Allegri. "The team will bounce back as they always have done. We lost against a great side and were missing a lot of players."
(Writing by Brian Homewood, editing by Pritha Sarkar)
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