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Arguably the most talented players considering similar periods of time. In each group order from the oldest to the youngest:

Years 1989-1991:
Code:
(1970) Andre Agassi       8  - 4  - 8 
(1970) Jim Courier        24 - 25 - 2 
(1971) Pete Sampras       84 - 5  - 5 
(1971) Goran Ivanisevic   40 - 9  - 16 
(1972) Michael Chang      5  - 15 - 15
Years 1999-2001:
Code:
(1980) Marat Safin        23 - 2  - 11 
(1980) Juan C. Ferrero    45 - 12 - 5 
(1981) Lleyton Hewitt     22 - 7  - 1 
(1981) Roger Federer      64 - 29 - 12 
(1982) Andy Roddick      [] - 158 - 14 *
Years 2009-2011:
Code:
(1990) Jerzy Janowicz     319 - 161 - 221
(1990) Milos Raonic       373 - 156 - 31 
(1991) Grigor Dimitrov    288 - 106 - 76
(1992) Ryan Harrison      360 - 173 - 79 **
(1992) Bernard Tomic      286 - 208 - 42
* Roddick appeared in the ranking for the first time in 2000, but he played two qualies to US Futures in 1998, and 3 Futures events in 1999.
** Harrison is No. 109 at the moment, his two compatriots born in 1992 (Sock & Kudla) in the Top 100, but in terms of experience Harrison is distinctively ahead of them now
 
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