Evidence from a systematic literature that we conducted previously revealed numerous inconsistencies in findings from the Pair Programming (PP) literature regarding the effects of personality on PP’s effectiveness. It also showed that, despite numerous investigations, the effect of differing personality traits of pairs on the successful implementation of pair-programming (PP) within a higher education setting is still unclear. In addition, our results also showed that the personality instrument used the most had been the Myers-Briggs Type Indicator (MBTI), despite being an indicator criticized by personality psychologists as unreliable in measuring an individual’s personality traits. These issues motivated our research, where we conducted a series of five formal experiments at the University of Auckland (between 2009 and 2010) using 594 undergraduate students as subjects to investigate the effects of personality composition on PP’s effectiveness. Our studies employed the Five-Factor personality framework, comprising five broad traits (Openness to experience, Conscientiousness, Extraversion, Agreeableness, and Neuroticism). Our experiments investigated three of the five traits - Conscientiousness, Neuroticism, and Openness. Our findings showed that Conscientiousness and Neuroticism did not present a statistically significantly effect upon paired students’ academic performance. However, Openness played a significant role in differentiating paired students’ academic performance. Participants survey results also indicated that PP not only caused an increase in satisfaction and confidence levels but also brought enjoyment to the tutorial classes and enhanced students’ motivation.