Jurgen Klopp’s Anfield debut ended in a frustrating draw against 10-man Rubin Kazan, as Liverpool registered their third successive 1-1 Europa League draw.

Zenit St Petersburg secured a narrow advantage in their Champions League last-16 tie against Benfica as Roman Shirokov’s brace helped the hosts to a hard-fought win at a frigid Stadion Petrovskiy last night.