Uber in June announced it was stopping food deliveries via its Uber Eats app in Italy due to lower-than-expected growth.
A joint statement from the NIdiL Cgil, Filcams Cgil and Filt Cgil unions said some 4,000 fully active riders lost their jobs.
But the Milan employment tribunal on Thursday "condemned Uber Eats Italy for anti-union conduct" for failing to properly consult trade unions, it said.
It said the company must withdraw the layoffs and begin talks with unions, in what it claimed was an "extraordinary" ruling.
"It is significant that for the first time the regulation of the relocation of multinationals is applied in Italy, which makes them responsible in the restructuring processes," the statement said.
"It is demonstrated once again that all the rights of employed workers must be applied to riders."
The 27 EU member states in June backed plans that could force companies like Uber and Deliveroo to treat workers as employees in a potential radical overhaul of the gig economy's business model.
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