| 8 Aug 2008 – 4 Feb 2009|
| Maccabi Tel Aviv (3rd title)|
Maccabi Tel Aviv F.C. (3rd title)
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. It was held in two stages. 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. Quarterfinals and Semifinals were held as two-legged matches, while the Final was one-legged match held at Ramat Gan Stadium. The defending champions were Maccabi Haifa. Maccabi Tel Aviv won the 2008–09 Toto Cup Al making it their third Toto Cup title overall.
2008–09 Toto Cup Al Wikipedia
The matches were played from August 8 to November 12, 2008.
The first legs were played on January 5 and 6, 2009 while the second legs were played on January 13 and 14, 2009.
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.