This paper studies on the Day-of-the-week effect by means of several binary classification algorithms in order to achieve the most effective and efficient decision trading support system. This approach utilizes the intelligent data-driven model to predict the influence of calendar anomalies and develop profitable investment strategy. Advanced technology, such as time-series feature extraction, machine learning, and binary classification, are used to improve the system performance and make the evaluation of trading simulation trustworthy. Through experimenting on the component stocks of S&P 500, the results show that the accuracy can achieve 70% when adopting two discriminant feature representation methods, including 'multi-day technical indicators' and 'intra-day trading profile.' The binary classification method based on LDA-Linear Prior kernel outperforms than other learning techniques and provides the investor a stable and profitable portfolios with low risk. In addition, we believe this paper is a FinTech example which combines advanced interdisciplinary researches, including financial anomalies and big data analysis technology.