Volandri, the runner-up in 2003 and 2004 who has never failed to reach the quarterfinals in five previous visits, won for the first time since Barcelona in April.
He led Cippola 6-1, 3-0 with a double break when Cippola briefly recovered and leveled at 3, but Cippola lost his serve again and didn't challenge Volandri.
Seventh-seeded Fabio Fognini, the only seed in action, won in debut in Umag by ousting 18-year-old Ricardas Berankis, a recent world junior No. 1, 6-3, 6-2. The Lithuanian wild card led 3-2 then lost seven games in a row in his second ATP event.
Boris Pashanski of Serbia saved five match points to defeat Gianluca Naso of Italy 6-3, 2-6, 7-6 (9).
Mathieu Montcourt of France defeated Antonio Veic of Croatia, 6-4, 6-2, achieving his first victory this season. Another Croatian, Roko Karanusic, advanced, ousting Italian qualifier Franceso Piccari 6-2, 6-2 for his maiden win in four visits to Umag.
The top four seeded players - Fernando Verdasco, Ivo Karlovic, Carlos Moya and Igor Andreev - had a bye in the first round.
Bilic Has No Complaints
French Open Show Court Schedules
Top-seeded Davydenko wins opener at Hypo