Derry City suffered penalty shoot-out heartache as their Europa Conference League campaign came to an end and it is Tobol who continue their adventure against Czech side Viktoria Plzen.
Brian Maher's penalty was kept out by his opposite number Ivan Konovalov, before Pavel Kireenko's sixth penalty ensured the Kazakhstan men secured a 6-5 victory.
Tobol had the chance to win the tie earlier in the shoot-out when Ben Doherty's effort was kept out by Konovalov, but Jovan Llic's effort from 12 yards came back off the bar, but it was Konovalov and Kireenko, who in the end played the big part in the shoot-out success.
The Brandywell men played superbly and controlled most of the 120 minutes and probably should have won the tie in the 90 minutes, as substitute Cian Kavanagh fired wide in stoppage time.
To their credit the 3,000 plus supporters who made the trip from Foyleside certainly made some noise and backed their team outstandingly.
After starting on the front foot, the Candystripes took the lead after Slovakia referee Peter Kralović pointed to the spot as he adjudged Ivan Rogač had fouled Micahel Duffy inside the box.
After the visitors' protests were waved away, City midfielder Will Patching calmly sent goalkeeper Konovalov the wrong way with the resulting spot-kick, side-footing home into the bottom right hand corner.
Derry were inches away from doubling their lead on 28 minutes as Jamie McGonigle teed up Duffy, but the left winger's 20-yard drive from the angle flashed just past Konovalov's left post.
Minutes later Tobol created their first real chance as Igor Ivanović showed good pace and strength to get away from Doherty, but his goal-bound cross-cum-shot was diverted over the bar by City defender Cameron McJannet.
Konovalov was called into action again just before the break, as the Russian net-minder easily held onto Patching's 20-yard curling free-kick.
Just before the hour mark a neat passing move by Tobol ended with the lively Ivanović finding space inside the box, but his curling left-footed shot was well off target.
Minutes later Patrick McEleney came off the bench to make his 50th appearance in European football, replacing the injured Patching and Cian Kavanagh came on for McGonigle.
Soon after Derry went close to scoring that crucial second goal as Paul McMullan's close-range shot was kept out by Konovalov's boot and the net-minder easily gathered another McMullan effort moments later.
Tobol missed a good chance to level things on the night as the Ivory Coast striker Serges Déblé got away from Doherty down the right, but his low shot was booted away by Maher.
Derry City 1-0 Tobol Kostanay (1-1 agg)
— RTÉ Soccer (@RTEsoccer) August 17, 2023
Kavanagh hits a glorious chance to win it wide in the sixth minute of injury time and we will have extra-time.
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With virtually the last kick of the game, Derry should have won the tie as Brandon Kavanagh found his namesake Cian, but the former Waterford youngster snatched at the clear cut opening and dragged his shot well wide from 12 yards with only Konovalov to beat.
Tobol played some neat passing on 96 minutes before Déblé chested the ball down inside the box to Miljan Vukadinović, but the Serbian winger's shot was straight at Maher. Neither side created much after Vukadinović's effort and the entertaining encounter was decided by penalties.
Derry City: Brian Maher, Ronan Boyce, Mark Connolly, Cameron McJannet, Ben Doherty; Sadou Diallo (Jordan McEneff 88), Adam O'Reilly (Cameron Dummigan 75), Will Patching (Patrick McEleney 64); Michael Duffy (Danny Mullen 111), Jamie McGonigle (Cian Kavanagh 64), Paul McMullan (Brandon Kavanagh 88)
Tobol Kostanay: Ivan Konovalov, Bagdat Kairov (Albert Gabaraev 90), Ivan Rogač, Bojan Mladović, Roman Asrankulov; Samat Zharynbetov (Yevhen Shakhov 76), Jovan llic, Serikzhan Muzhikov (Pavel Kireenko 84); Igor Ivanović (Ramazan Orazov 76), Serge Déblé (Pavel Zabelin 113), Miljan Vukadinović
Referee: Peter Kralović (Slovakia)
Tobol Kostanay beat Derry City 6-5 on penalties
— RTÉ Soccer (@RTEsoccer) August 17, 2023
The Candystripes' dream of the Europa Conference League group stages ends in cruel fashion
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