Matt Ritchie was injured in Newcastle United's defeat to Leicester City and will be out of action until October, Steve Bruce confirmed.
Preston North End will host EFL Cup holders Manchester City in the third round after Wednesday's draw.
League Two sides Crawley Town and Colchester United shocked their Premier League opponents in the EFL Cup.
Gary Neville was thrilled after Salford City were paired with Leeds United in the first round of the EFL Cup.
Jurgen Klopp has had a miserable record in major finals but his trophy drought is at an end.
Liverpool are favourites to lift the Champions League at Tottenham's expense but Jurgen Klopp's record in finals makes for grim reading.
Vincent Kompany confirmed his impending Manchester City departure on Sunday, but Pep Guardiola expects he will be back sooner or later.
Manchester City only failed to win one trophy - the Champions League - this season and Bernardo Silva hopes to put that right next term.
Manchester City's trophy parade on Monday included the departing Vincent Kompany saying farewell before he returns to Anderlecht.