Leroy Sane's potential transfer to Bayern Munich hit another snag as he was taken off injured in the Community Shield.
Man City were forced into a change after just 11 minutes as Sane went down with an Achilles problem following a tangle with Liverpool's Trent Alexander-Arnold.
An injury poses a serious threat to any potential transfer deal, if he is going to leave City this summer.
Bayern remain determined to get a deal done, although City are asking for a whopping £145million to let the winger go.
Sane is still an integral part of Manchester City's plans for the new season and Pep Guardiola has openly spoken about his desire to keep him at the Etihad.
Bayern, however, are determined to get the deal done.
Sane was included in the City squad for the Community Shield clash with Liverpool at Wembley on Saturday and Guardiola named him in the starting XI, reiterating his intention to use him as a key man.
But it all went wrong just 11 minutes into the game following his collision with Alexander-Arnold.
San appeared to land awkwardly on his leg, causing damage to his Achilles tendon.
After a minute of treatment from the physios, it was decided that he would have to be taken off and he was replaced by Gabriel Jesus.
Bayern have until the end of August to complete a deal, with the Bundesliga transfer window not ending for another four weeks.
Robert Lewandowski, the Bayern striker, has called on his side to get big name deals done this summer.
"Sure, the young players on the bench have potential, that's true - but sometimes you need direct reinforcement from someone who can come in and help the team," Lewandowski said.
"My opinion remains the same, because today was precisely the right time where we could have looked and seen what could happen if we had such a professional player ready to come on."
