Scotland's euphoria at beating France on Saturday started to evaporate on a difficult evening here in Kiev last night when a brave defensive performance against a powerful Ukraine side was undone in the final half hour.
A succession of good chances had been missed by Oleg Blokhin's side before in the 60th minute Scotland's failure to deal with a free-kick saw Olexander Kucher beat the outstanding Craig Gordon in goal from close-range. It got worse for the visitors after Kenny Miller missed a golden chance to equalise in the 80th minute, putting a header well wide when unmarked in the penalty area. Steven Pressley was then sent off for a professional foul on Andrei Shevchenko as he threatened to go clear on goal. Then with two minutes to go Robbie Neilson was harshly judged to have fouled Shevchenko in the area, the Chelsea striker scoring from the penalty.
"We are disappointed," Walter Smith, the Scotland manager, said. "We rode our luck a bit when they hit the post and then had another opportunity.
"I thought we were over the worst of that but they got a goal and we missed our best chance," he added. "I don't think anyone can fault the players, they are giving their all."
The defeat ends Scotland's 100 per cent start to Group B and further problems will preoccupy Smith with Pressley, James McFadden and Darren Fletcher - who were both booked - all suspended for the next match against Georgia in March.
Scotland had managed to get to half-time still level after Ukraine squandered a number of good opportunites. Gordon held a header from Maxim Kalinichenko before the Spartak Moscow midfielder put a powerful header just over the bar.
It looked like it would be one of those nights for the hosts two minutes into the second half when Shevchenko bundled his way through and squeezed the ball under Gordon only for it to hit the post.
However, Scotland's defence finally cracked on the hour. Shevchenko floated a free-kick into the box and James McFadden's attempted clearance came off Vyacheslav Sviderskiy and broke to Kucher, who drilled low into the net.
Ukraine (3-5-2): Shovkovskiy (Dynamo Kiev); Nesmachniy (Dynamo Kiev), Sviderskiy (Arsenal Kiev), Rusol (Dnipro); Kucher (Shakhtar Donetsk), Tymoschuk (Shakhtar Donetsk), Shelayev (Dynamo Kiev), Gusev (Dynamo Kiev), Kalinichenko (Spartak Moscow); Shevchenko (Chelsea), Voronin (Bayer Leverkusen). Substitutes used: Milevskiy (Dynamo Kiev) for Gusev, 62; Vorobey (Shakhtar Donetsk) for Kalinichenko, 76; Shershun (Dnipro) for Voronin.
Scotland (4-5-1): Gordon (Hearts); Neilson (Hearts), Caldwell (Celtic), Weir (Everton), Pressley (Hearts), G Alexander (Preston North End); Ferguson (Rangers), Fletcher (Manchester United), Hartley (Hearts), McFadden (Everton); Miller (Celtic). Substitutes used: Boyd (Rangers) for McFadden, 72; McManus (Celtic) for Neilson, 88.
Referee: M Hansson (Sweden).Reuse content