Roma, whose only achievement of note in the European Cup was being runners-up in 1984, were overjoyed at getting through and avoiding the big guns but now even the inexperienced Ukrainians seem to represent a mighty hurdle.
Three games without a win in Serie A have come at the same time as the club's ownership situation has looked like being resolved with an American consortium in talks to buy the cash-strapped outfit.
Both the poor performances, which have left last season's Italian runners-up in eighth spot, and the possibility new owners might want someone else in charge have put coach Claudio Ranieri under pressure and fans have even protested at training.
"I don't see a spark. There's not the enthusiasm or organisation on the field of last season. It's certainly my fault because I am the boss," Ranieri told reporters following Saturday's 2-0 home league defeat by second-placed Napoli.
Another sticking point has been Ranieri's deteriorating relationship with captain Francesco Totti, a hero among Roma's fanatical supporters for staying with the club all his career.
The 34-year-old striker is now a shadow of his former self and is no longer guaranteed a start with Marco Borriello and Mirko Vucinic offering more speed and power.
"He's just come back from having 'flu, he wasn't ready to start," Ranieri said with Totti on the bench against Napoli.
To get fans back on side, Ranieri is likely to select Totti against the Ukrainians while France centre-back Philippe Mexes and Argentina's Nicolas Burdisso are back from domestic bans to relieve the recently error-prone Juan. Adriano is injured.
WINTER BREAK
The Ukraine league's winter break from November to March 5 means Shakhtar have not played an official match since December 8 when they defeated Sporting Braga 2-0 to top the group and progress to the Champions League last 16 for the first time.
The big-spenders have played nine friendlies, winning four, during the break but have not recruited any new players.
Their heaviest defeat came at the Dubai Cup where they lost 5-2 to Slovakia's MSK Zilina, sparking criticism at home.
Vasyl Kobin will miss the first leg because of an Achilles tendon injury as will Olexandr Kucher with a knee problem.
Influential Brazilian midfielder Fernandinho is back from a broken leg but coach Mircea Lucescu only expects him to be fully fit for the second leg against Roma in Donetsk on March 8.
Probable teams:
AS Roma: 27-Julio Sergio; 77-Marco Cassetti, 4-Juan, 5-Philippe Mexes, 17-John Arne Riise; 30-Simplicio, 16-Daniele De Rossi, 20-Simone Perrotta; 94-Jeremy Menez; 10-Francesco Totti, 22-Marco Borriello
Shakhtar Donetsk: 30-Andriy Pyatov; 33-Darijo Srna, 27-Dmytro Chygrynskiy, 44-Yaroslav Rakitskiy, 26-Razvan Rat; 19-Olekiy Gai, 29-Alex Teixeira; 20-Douglas Costa, 8-Jadson, 10-Willian; 9-Luiz Adriano.
Referee: Olegario
