This study investigated the effects of harvesting at different plant maturation stages on the fruit and essential oil yield as well as its compositions of anise. It was carried out at El- Baramoon Research Farm, Mansoura Horticulture Research Station, HRI, ARC, Egypt, during the winter seasons of 2013/2014 and 2014/2015. The plants were harvested at eight different fruit development stages and determinations were made of the yields of fruit , germination percentage the thousand fruit weight (seed index), the essential oil percentage and its constituents. The obtained results indicated that high yield and quality of anise fruits were obtained when fruits harvested at stage 4 (the primary umbel was matured completely).The highest essential oil percentage was higher in stage 1 (the primary umbel was at the beginning of waxy stage.). However, this high percentage of essential oil did not produce the maximum oil yield per plant in stage1 was associated with low fruit yield. Essential oil yield per plant with high Trans-Anethole content reached their maximum when fruits harvested at stage 4. Generally, it could be recommended that to obtain the maximum fruit yield and quality as well as high essential oil yield with high Trans-Anethole content, anise fruits should be harvested at stage 4 (The primary umbel was matured completely).