Oeiras, Portugal:Third-seeded Novak Djokovic struggled to beat Igor Andreev 6-2, 4-6, 7-6 (5) in the first round of the Estoril Open on Monday.
On the same day he moved to a career-high No 5 ranking, the 19-year-old Djokovic missed a match point at 5-4 in the third set and two more in the tiebreaker before finishing off Russia's Andreev, on a comeback from knee surgery, in 2 hours, 40 minutes.
Djokovic is chasing his third title of the season, after winning in Adelaide in January and the Miami Masters a month ago.
Juan Monaco of Argentina knocked out eighth-seeded Gael Monfils 7-5, 1-6, 6-2, extending the miserable run for the Frenchman, who hasn't won since the Australian Open.
In another upset local player Frederico Gil triumphed over Ruben Ramirez Hidalgo of Spain 6-1, 4-6, 6-3.
Also, Juan Martin del Potro of Argentina rallied past Alejandro Falla of Colombia 1-6, 6-2, 6-4, and avenged a loss at the U.S. Open, Spanish qualifier Santiago Ventura beat Argentina's Sergio Roitman 7-5, 6-2, and Russian Evgeny Korolev retired feeling unwell after losing eight of nine games to Spain's Alberto Martin.
In the women's first round, third-seeded Lucie Safarova of the Czech Republic beat Aravane Rezai of France 7-6 (5), 7-5.
Fifth-seeded Olga Poutchkova defeated fellow Russian Anastasia Rodionova 6-3, 4-6, 7-6 (5) and will try to win consecutive matches for the first time this year when she plays Nuria Llagostera Vives of Spain, a 6-1, 7-6 (2) winner over Portugal wild card Ana Catarina Nogueira.
Victoria Azarenka of Belarus defeated Virginie Razzano of France 7-6 (14), 7-5.