Roger Federer had picked up his first big cheques in the first half of 2002 when he reached the final in Miami and won the maiden Masters 1000 title in Hamburg, finishing that season on almost $2,000,000 of prize money and doubling that in 2003 after winning the first Major crown at Wimbledon. In the next five years, Roger was the dominant figure on the court and he earned more and more money to move closer to Pete Sampras' record in that category.

The 14-time Grand Slam champion had earned $43,280,489 in his illustrious career and Roger managed to overcome him when he defeated Jo-Wilfried Tsonga in the third round of Madrid Masters in 2008 to become the most paid mail player in the history of the game! The Swiss could win only one Grand Slam title that year but he did enough to grab more than $5,000,000 for the fifth season in a row ($1,500,000 at the US Open alone) and leave the American behind him.

Federer took some well-deserved rest after lifting the fifth straight title in New York, playing only one Davis Cup match before returning in Madrid where he won the crown two years earlier. In the second round, Federer defeated Radek Stepanek without facing a break point and he fends off all four against Tsonga to reach the quarter-final and achieve another milestone that put him ahead of Sampras.

The match lasted 63 minutes and Tsonga took just five games, winning just 12 points on the return and suffering three breaks of serve to send Federer into the last eight. There, Roger played another rock solid match to oust Juan Martin del Potro 6-3 6-3 before losing to Andy Murray 3-6 6-3 7-5 in the semis, missing a chance to reach another Masters 1000 final.

A lot has changed since the time of Pete Sampras' prime years and three more players have managed to pass him on the ATP Prize Money Leaders list, although it will be remembered that Pete Sampras did that first on this day 10 years ago.

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