On 16 February 2009, the Radwańska sisters played their first official tour match against each other in the first round of the Barclays Dubai Tennis Championships.
Urszula won the match in straight sets 6–4, 6–3 hitting six aces and 25 winners.

At the BNP Paribas Open in Indian Wells, she defeated sixth-seeded Svetlana Kuznetsova in three sets, the highest ranked player she had ever defeated.
She then lost to ninth-seeded Caroline Wozniacki in her first ever WTA fourth-round match.
Her results at this tournament caused her singles ranking to break into the top 100 for the first time.

In the second Grand Slam tournament of the year, the French Open, Radwańska lost in the first round to Belgian Yanina Wickmayer.
She advanced to the second round of the Wimbledon Championships, falling to No.
14, Dominika Cibulková.
She then competed in the US Open, losing to Kristina Barrois in the opening round.
On 16 February 2009, the Radwańska sisters played their first official tour match against each other in the first round of the Barclays Dubai Tennis Championships. Urszula won the match in straight sets 6–4, 6–3 hitting six aces and 25 winners.
At the BNP Paribas Open in Indian Wells, she defeated sixth-seeded Svetlana Kuznetsova in three sets, the highest ranked player she had ever defeated. She then lost to ninth-seeded Caroline Wozniacki in her first ever WTA fourth-round match. Her results at this tournament caused her singles ranking to break into the top 100 for the first time.
In the second Grand Slam tournament of the year, the French Open, Radwańska lost in the first round to Belgian Yanina Wickmayer. She advanced to the second round of the Wimbledon Championships, falling to No. 14, Dominika Cibulková. She then competed in the US Open, losing to Kristina Barrois in the opening round.
Urszula Radwańska