Kenikir (Cosmos caudatus) is an Indonesian aromatic herbal plant that are widely consumed as salad and commonly used as traditional medicinal herbs which is known to possess several beneficial functional properties, such as antioxidant and anti-diabetic properties which are contributed by high content of bioactive compounds such as flavonoids and phenolic compounds in kenikir leaves. Blanching is one of the commonly used pre-treatments to inactivate enzyme in vegetables and could increase the total phenolic content and antioxidant activity. Extraction is a process to separate the desirable compound from plants with the usage of solvent. The most suitable solvent in aromatic compound extraction are polar and semi-polar solvents, such as ethanol and ethyl acetate. Therefore, a research need to be done to determine the best type of pre-treatment and extraction solvent towards the phytochemical and functional properties of kenikir leaves. This research was performed in complete randomized design of two factors which were the pre-treatment (fresh and blanch) and extraction solvent (ethanol 70%, ethanol 96%, and ethyl acetate). The results showed that the best type of pre-treatment and extraction solvent was fresh kenikir leaves extracted with ethanol 70 % solvent which had 37.63 ± 6.78 mg GAE/g phenolic content, 28.59 ± 1.38 mg QE/g flavonoid content, 2207.33 ± 586.29 ppm antioxidant activity, and 808.10 ± 382.43 ppm anti-diabetic activity.