Liverpool were drawn in a testing Champions League group as they attempt to move on from defeat in last season's final.
Liverpool's flirtation with a historic quadruple last season feels a distant memory after a rocky start this term, not helped by a string of injuries. Jurgen Klopp has guided the Reds to three of the past five Champions League finals, but only once come away with the trophy.
Ajax are going through a period of transition after the departure of Erik ten Hag to Manchester United and the habitual loss of key players.
Napoli made a run at the Serie A title before fading badly down the stretch, but in Victor Osimhen they have one of the game's most exciting young attackers.
Rangers are back at this stage for the first time in 12 years, having climbed back from the Scottish fourth tier after going into liquidation.