The purpose of this study was to investigate the differences of individual characteristics, the technical performance and the different courts for male singles players of the Grand Slams between 1995 and 2008. Data were collected from ATP official website which provided the competition records of the Grand Slams spanned from 1995 to 2008. The statistical methods of descriptive analysis and one-way ANOVA were applied to analyze the data. The major conclusions of the research were as follows: Firstly, there were clear rises in all age, height, years of experience for male single players of the Grand Slams in different generation.; second, the skill of serving and receiving showed a significant difference for male singles player of the Grand Slam in different generation; and lastly, the skill of serving and receiving showed a significant difference for male singles player of the Grand Slam due to the variation of competition courts. Based on the above findings, young tennis players and coaches could make a tailored training schedule targeting at participation in the Grand Slam in the future.