Liverpool 1 Rubin Kazan 1: Klopp's men struggle against 10-man visitors
Jurgen Klopp endured a frustrating debut in the Anfield dugout as Liverpool were held to a disappointing 1-1 Europa League draw by 10-man Rubin Kazan on Thursday.
The German manager was forced to settle for a share of the spoils for the second consecutive game despite his side having an extra man for over half of the match.
Marko Devic gave Rubin a first-half lead with a brilliantly-taken goal, but Oleg Kuzmin's red card appeared to have ended the Russians' chances of picking up a positive result.
Emre Can smashed home an equaliser before half-time, but Liverpool were extremely poor in the second half as the returning Christian Benteke hit the post in one of their few clear-cut opportunities.
The Reds have now drawn all three of their Europa League games, but stay second in Group B after leaders Sion beat Bordeaux in the other game.
Joe Allen came in for Lucas Leiva in Klopp's only change from the goalless Premier League draw at Tottenham, while Benteke and Roberto Firmino – who have been out for a month – returned to the substitutes' bench.
Can took a pass from Allen and curled an early effort into the side netting, but it was the visitors who moved into a surprise lead after 15 minutes.
Rubin captain Kuzmin went past Can and floated a delivery into the area from the right. Devic got goal-side of Nathaniel Clyne, showing strength to control with his chest and flick an impressive finish into the far corner.
The hosts tried to make a swift response when Adam Lallana sent an effort wide from the edge of the box, before the Southampton star flicked an impressive header just over from Philippe Coutinho's free-kick.
Coutinho himself threatened next when he seized on a poor pass from Magomed Ozdoev, only to fire wide with his left foot after a promising run had given him a decent chance.
A crucial three moments in the game then took place in quick succession. Rubin came close to making it two when Gokdeniz Karadeniz found Blagoy Georgiev in space inside the area, but the in-form Simon Mignolet reacted well to tip his shot over.
Then Kuzmin was given his marching orders. Having already been booked for a high tackle on Alberto Moreno, he received a second yellow card for a clear body-check on Can.
And the visitors were punished instantly as Coutinho whipped in a free-kick from the left that was headed down by Divock Origi, allowing Can to power an effort into the roof of the net from a yard out.
Despite their numerical advantage, Liverpool did not create much of note in the early stages of the second half.
Coutinho drove a free-kick wide and was then off target with another effort after being set up by a driving James Milner run.
Klopp took swift action to try to lift his team, replacing the disappointing Coutinho with the returning Benteke having already introduced Lucas in place of Allen at the break.
Benteke had a chance to score as the game entered the final 20 minutes, but volleyed wide from Clyne's cross as Klopp brought on Firmino in his final effort to inspire a victory.
Can then forced Sergei Ryzhikov into a solid save with a bouncing left-footed shot, the Rubin goalkeeper's first work of the second half.
Benteke came closest to finding the winner, receiving a pass from Lallana and guiding a low shot across the face of goal that struck the foot of the post as Klopp got another insight into the size of the task he has undertaken.