Tennis federations are regularly faced with decisions regarding which athletes should be supported in financial terms, and for how long. The financial investments can be considerable, given the cost of competing on tour has been estimated at a minimum $121,000 per year and only the top 130 professionally ranked athletes earned enough prize money to cover this cost in 2012. This study investigates key points of progression in tennis players' careers, to determine how these have changed over time and how that evolution may inform talent development. Approximately 400,000 weekly rankings for 273 male professional tennis players between 1985 and 2010 were compiled, and historical trends in the time taken to reach career milestones were investigated by least-squares regression. The time between earning a first professional ranking point and entry into the Top 100 significantly increased over time for all considered athletes. This was at the detriment of time spent within the Top 100 for some athletes. Career peak Top 50-100 athletes have shown an increase in longevity. These results assist tennis federations in assessing the progress of developing athletes and highlight the evolving nature of the competition for top players.