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Monza captain Matteo Pessina faces a lengthy spell on the sidelines after undergoing surgery on a serious knee injury.
A sensational reunion could be on the cards as Di Gregorio's Juventus future hangs in the balance.
The Italian season starts with four Coppa Italia first round ties, all decided on the day.
Napoli's €20m flop could get a Serie A lifeline as Monza come calling.
Monza will be without their captain for a significant period after he suffered a serious knee injury.
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BBC Sport · 19 Aug 2026