They actually lost thrice - in 2017 TFL pulled their PHV licence because Uber London Limited wasn't considered to be a 'fit and proper person', Uber thought they could brazen it out only to find that TFL is beholden only to the Mayor and they ended up having to come back on bended knee, and then it was further refused in 2019 but returned on appeal -
https://www.judiciary.uk/wp-content/uploads/2020/09/Uber-v-T...), which lists significant failings by Uber that they had since remedied.
The third outing with the Supreme Court was about employment rights - were the drivers workers, or genuine independent contractors for whom Uber are merely acting as a booking agent (which the Uber model relies almost entirely on).
The Employment Tribunal, The Employment Appeal Tribunal, The Court of Appeal and finally the Supreme Court all said "nah fam, you ain't fooling nobody" and the original ET was especially scathing:
> It seems to us that the Respondents' general case and the written terms on which they rely do not correspond with the practical reality. The notion that Uber in London is a mosaic of 30,000 small businesses linked by a common 'platform' is to our minds faintly ridiculous. In each case the 'business' consists of a man with a car seeking to make a living by driving it.
The third outing with the Supreme Court was about employment rights - were the drivers workers, or genuine independent contractors for whom Uber are merely acting as a booking agent (which the Uber model relies almost entirely on).
The Employment Tribunal, The Employment Appeal Tribunal, The Court of Appeal and finally the Supreme Court all said "nah fam, you ain't fooling nobody" and the original ET was especially scathing:
> It seems to us that the Respondents' general case and the written terms on which they rely do not correspond with the practical reality. The notion that Uber in London is a mosaic of 30,000 small businesses linked by a common 'platform' is to our minds faintly ridiculous. In each case the 'business' consists of a man with a car seeking to make a living by driving it.