Amkar Perm became the first Russian Premier League club to suffer a cup upset this season with an extra-time defeat to second-tier side SKA-Energia Khabarovsk in the fifth round on Tuesday.

Amkar coach Nikolai Trubachev had made ten changes to the starting lineup from Amkar’s 3-2 league defeat to Dynamo Moscow, fielding a host of young Russian players against a SKA-Energia side who are contenders for promotion to the Premier League.

SKA-Energia striker Evgeny Lutsenko put paid to Amkar’s cup hopes with a 102nd-minute strike after the match in Russia’s Far East finished 1-1 in normal time.

Amkar midfielder Artur Ryabokobylenko had kept his team in the tie with an 82nd-minute goal that canceled out Robert Arzumanyan’s 16th-minute opener for hosts SKA-Energia.

Trubachev brought on senior players Nikolaos Karelis and Pavel Ignatovich in the second half, but the strikers proved unable to turn the tide.

Later Tuesday, recently relegated Spartak Nalchik host Premier League side Terek Grozny, before Russian champions Zenit St. Petersburg travel to Baltika Kaliningrad.

Wednesday sees 10 games with all four major Moscow teams in action, before three ties Thursday.