The 2008–09 Toto Cup Al was the twenty-seventh season of the third most important football tournament in Israel since its introduction and fifth under the current format.

First, twelve Premier League teams were divided into three groups.

The winners and runners-up, as well as two best third placed teams from each group, advanced to the Quarterfinals.

The first game between Ironi Kiryat Shmona and Bnei Sakhnin (that should have been played in Kiryat Shmona) has been cancelled due to safety reasons during the 2008–2009 Israel–Gaza conflict.

The tie was eventually played as one-legged match on a neutral ground (Ramat Gan Stadium, Ramat Gan) on January 20, 2009.