Too many injuries were bound to end in Arsenal's first group defeat in Kiev last night. And so it proved as the English Premiership champions dropped from top to the bottom of the table and saw their chances of reaching the quarter-finals severely weakened.
An Arsenal team that would have not looked out of place in the League Cup started minus not only Dennis Bergkamp, Tony Adams and Marc Overmars, but Nicolas Anelka, a late withdrawal with a damaged toe.
When Adams's replacement and stand-in captain Steve Bould limped off near half-time with a hamstring injury, the task facing Arsene Wenger's patched-up heroes became just too much.
Three goals, all from the old Arsenal speciality set-pieces, gave Kiev a comfortable win as they took full advantage of their opponents' depleted circumstances.
Arsenal created enough chances to have scraped at least a priceless draw, but the lack of quality of two of the stand-ins, Luis Boa Morte and Christopher Wreh, let them down.
Boa Morte, starting only his second match of the season, replaced Overmars on the left wing while Nelson Vivas came into midfield. Ray Parlour took up the Bergkamp role just behind Wreh, the main striker who was making only his third start this season.
But nearly everything that could have gone wrong for Arsenal did. Their spirit was fine but they simply lacked the collective quality to beat a team which showed their pedigree at Wembley two weeks ago.
Arsenal created the early openings. On 14 minutes, Boa Morte scuffed a shot wide from an inviting position; then Wreh, near the penalty spot, had time and space to find the net instead of the advancing arms of the goalkeeper.
Olexander Shovkovskyi then saved well from Martin Keown's header, but on 26 minutes the defender had greater cause for dismay when he gave away the penalty which gave Kiev the lead.
Sergei Rebrov broke down the left with Keown in pursuit. Deep in the area he brought down the Ukrainian and the scorer of Kiev's late equaliser at Wembley converted the spot-kick, though only just; David Seaman pushed the ball up above his shoulder, but it trickled over the line.
Kiev were now rampant. Yuri Dmytrulin saw a goal-bound shot blocked by two desperate defenders; then Seaman darted from his line to deny Andrei Shevchenko.
Arsenal came back as the break approached, but again the chances were squandered, Wreh heading another inviting chance wide and Patrick Vieira seeing his promising shot saved by the 'keeper.
But there was still hope. Two minutes into the second half Emmanuel Petit, recovered from a throat infection, curled in a free-kick which Vieira got a touch to at the far post. But Shovkovskyi made another important save.
Kiev, however, soon reminded Arsenal they were not sitting on their lead. Shevchenko forced a diving save from Seaman and then, on 62 minutes, Kiev went further ahead. Winterburn gave away a freekick which Oleh Luzhnyi directed perfectly on to the head of Olexander Holovko who, near the penalty spot and with some help from Vivas, guided the ball past a rooted Seaman.
Holovko nearly turned villain two minutes later when he headed Vivas's cross firmly towards his own goal. A startled Shovkovskyi's tipped the ball over.
On 72 minutes, Kiev scored a third. Arsenal gave away another free kick, through Vivas's foul, and Shevchenko rifled a 25-yard shot past Seaman's right hand.
Near the end Hughes pulled one back, heading in Petit's corner, and in the 88th minute Wreh saw a seemingly good effort disallowed. Arsenal now have two games - home to Lens and away to Panathinaikos - to repair the damage and hope for favourable results elsewhere. It is a daunting prospect. Arsene Wenger heaped praise on his patched-up side, despite their first defeat in the competition, and said he felt they still had a fighting chance of reaching the quarterfinals.
"I think Kiev are in a very good position now because they won by two clear goals and the group is very tight," the manager said. "But I am proud of my team for the way they kept working and fighting for 90 minutes. It will be difficult now but we still have a chance to go through."
Wenger drew attention to the players that were missing, emphasising: "It was difficult to imagine going into a game like this without Dennis Bergkamp, Tony Adams and Marc Overmars. Then we lost Nicolas Anelka today with an infected foot. People keep saying I should buy more strikers, but to cover a situation like this I would need to buy 10. The biggest disappointment here was that we conceded goals to a penalty and two free kicks, but we gave an excellent Kiev side a real fight throughout the game."
Arsenal's defeat also brought more injury problems. Acting captain Bould had to be substituted with a hamstring injury and could be out for three weeks. Bould had collected a cut in his head which needed two stitches, but Wenger confirmed: "It was the hamstring which forced him to come off."
With Wenger worried that his regular captain Adams would be out for two more weeks with a back injury it leaves the champions desperately short for a critical programme next week.
They are home to Everton in the Premiership on Sunday and then face a midweek League Cup derby against Chelsea before a collision with George Graham's Tottenham Hotspur three days later.
Manchester United European Cup odds have been cut from 8-1 to 9-2 second favourites by William Hill who make Inter Milan 4-1 favourites, but have lengthened Arsenals odds from 7-1 to 20-1.
Dynamo Kiev: Shovkovsky, Luzhnyi, Horovko, Vashchuk, Dmytrulin, Kossovsky, Shevchenko, Rebrov, Husin, Kardash, Belkevitch (Kalitvintsev 89). Subs Not Used: Kernozenko, Gurerassimenko, Mikhailenko, Makouski, Kiriukhin, Venglinski. Booked: Vashchuk. Goals: Rebrov 26 pen, Horovko 61, Shevchenko 72.
Arsenal: Seaman, Dixon, Winterburn, Vieira, Bould (Grimandi 44), Vivas (Garde 85), Wreh, Keown, Parlour, Petit, Boa Morte (Hughes 65). Subs Not Used: Manninger, Upson, Grondin, Riza. Booked: Winterburn, Vieira, Keown, Vivas. Goals: Hughes 84. Att: 80,000.
Referee: P Ceccarini (Italy).