The 2008–09 Toto Cup Artzit was the 10th time the cup was being contested. This was the last edition of the third division Toto Cup, as Liga Artzit was dissolved at the end of the season.
For this season, the 12 Liga Artzit clubs were divided into three groups with four clubs in each group. The three group winners, together with the best runner-up advanced to the semi-finals.
Source: Toto Cup Artzit 2008/2009 IFA (in Hebrew) Rules for classification: 1st points; 2nd goal difference; 3rd matches won; 4th goals scored; 5th head-to-head; 6th decision match (A) Advanced to the Semifinals Notes:
Source: Toto Cup Artzit 2008/2009 IFA (in Hebrew) Rules for classification: 1st points; 2nd goal difference; 3rd matches won; 4th goals scored; 5th head-to-head; 6th decision match (A) Advanced to the Semifinals Notes:
Source: Toto Cup Artzit 2008/2009 IFA (in Hebrew) Rules for classification: 1st points; 2nd goal difference; 3rd matches won; 4th goals scored; 5th head-to-head; 6th decision match (A) Advanced to the Semifinals