A commonly held opinion is that left-handed tennis players are overrepresented compared to the percentage of left-handers within the general population. This study provides the domain insights supported by data analysis that could help inform the decision of parents and coaches considering whether a child should start playing tennis as left- or right-handed when there is no strong arm-handed dominance. Compared to the commonly cited figure of about 10% of left-handed male population, data analysis from the official ATP web site for the top 100 ranked tennis players over the past decades (1985-2016) shows evidence of overrepresentation of left-handed elite tennis players (about 15%). The insights and data analysis can inform the handedness decision, advance coaching and strategic game concepts, enhance media coverage/analytics, left-handed facts and statistics, and inform tennis equipment manufacturing.