Fiorentina must overcome Sporting Lisbon if they are to return to the UEFA Champions League group stage following the draw for the play-off round in Nyon.
Unseeded under UEFA's new qualifying format, Fiorentina avoided being paired with the likes of Arsenal, Lyon, Stuttgart and Panathinaikos.
Cesare Prandelli's side will travel to Lisbon for the first leg on August 18/19, before hosting the crucial return in Florence on August 25/26.
The Viola will join Serie A champions Inter, Juventus and AC Milan in the group stage if they can overcome their Portuguese Liga opponents over the two legs.
Elsewhere in the non-Champions section of the play-off draw, Arsenal and Celtic go head-to-head in an all-British tie, Lyon welcome Belgian giants Anderlecht, Panathinaikos host Atletico Madrid and Stuttgart travel to Romanian outfit Timisoara.
There are also five group stage places for the other half of the draw. The Champions section paired Greece's titleholders Olympiacos against Sheriff from Moldova, while Austria's Salzburg take on Maccabi Haifa of Israel. Ventspils, bidding to become the first Latvian side to reach the competition's group stage, must overcome Swiss giants Zurich, Denmark's Copenhagen take on Apoel Nicosia from Cyprus and Levski Sofia of Bulgaria are the opponents for Hungary's Debrecen.
The ten losing teams will automatically drop into the inaugural UEFA Europa League group stage.
UEFA Champions League 2009-10
Play-off Round: Non-Champions Path
First leg: Tuesday 18 August
Celtic (SCO) v Arsenal (ENG)
Sporting Lisbon (POR) v Fiorentina (ITA)
Timisoara (ROU) v Stuttgart (GER)
First leg: Wednesday 19 August
Lyon (FRA) v Anderlecht (BEL)
Panathinaikos (GRE) v Atletico Madrid (ESP)
Second leg: Tuesday 25 August
Anderlecht v Lyon
Atletico Madrid v Panathinaikos
Second leg: Wednesday 26 August
Arsenal v Celtic
Fiorentina v Sporting Lisbon
Stuttgart v Timisoara
Play-off Round: Champions Path
First leg: Tuesday 18 August
Copenhagen (DEN) v Apoel Nicosia (CYP)
Sheriff (MDA) v Olympiakos (GRE)
First leg: Wednesday 19 August
Levski Sofia (BUL) v Debrecen (HUN)
Salzburg (AUT) v Maccabi Haifa (ISR)
Ventspils (LVA) v Zurich (SUI)
Second leg: Tuesday 25 August
Debrecen v Levski Sofia
Maccabi Haifa v Salzburg
Zurich v Ventspils
Second leg: Wednesday 26 August
Apoel Nicosia v Copenhagen
Olympiakos v Sheriff
Source: UEFA
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