Jose Mourinho suffered his first ever home defeat in Serie A after Roma slipped to a 2-1 loss to AC Milan on Sunday.
The wait for a win over a big side has been prolonged after Roma failed to get going against a team quickly pulling away from them both on the day and in the season.
Milan took the lead through a Zlatan Ibrahimovic free kick in the first half and doubled it via a Franck Kessie penalty in the second.
A red card shown to Theo Hernandez midway through the second half meant Roma had a man advantage, but they could not utilise it.
Their consolation came from Stephan El Shaarawy in stoppage time, but despite a burst of pressure that followed, it was too little too late.
Roma remain in the top four for now, but as long as they struggle against other teams trying to aim there, it will be an uphill battle to remain in such territory.
They will be hoping to get back on track in games against Bodo/Glimt and Venezia in the Europa Conference League and Serie A in the week coming up.
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