Chinese herbal medicine (CHM) is a commonly used complementary and alternative medicine for patients with chronic liver diseases in Taiwan. In order to identify how CHM is prescribed for patients with chronic liver diseases, the drug effectiveness was used to classify the herbal formulae. The aim of this study is to explore the prescription pattern of drug effectiveness and the factors that affect this pattern. The National Health Insurance (NHI) database was analyzed for the pharmacoepidemiology study. Traditional Chinese medicine (TCM) outpatients who were identified by Gastroenterology with chronic liver diseases in the year of 2008 were included. Statistics and data mining tools were employed to explore CHM prescription pattern and factors that affect the pattern in terms of drug effectiveness, respectively. Among the 43,119 subjects treated chronic liver diseases with CHM, herbal formulae that has the effect of He Jie (harmonize, 63.7%) and Qing Re Xie Huo (clear heat and drain fire, 40.8%) were most commonly prescribed. Subjects prescribed for formulae with the effects of Fa Biao (release exterior, 45.4 years) and Qu Feng (expel wind 52.0 years) were the youngest and eldest, respectively. Male were more commonly prescribed for Bu Yang (tonify and nourish), Qing Re Xie Huo, and Li Xue (regulate blood); female were more commonly prescribed for He Jie, Biao Li (exterior and interior), and Ren Zao (moisture dryness). This study shows the prescription pattern of CHM in terms of drug effectiveness for chronic liver diseases. Gender and age affect this pattern.