Andy Roddick advanced when Philipp Kohlschreiber retired 6-3 2-1 in the Shanghai Masters round of 64. Andy Roddick extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-08-14 | Cincinnati Masters | R64 | hard | Philipp Kohlschreiber | 6-7 7-5 6-1 |
| 2010-06-21 | Wimbledon | R32 | grass | Andy Roddick | 7-5 6-7 6-3 6-3 |
| 2008-01-14 | Australian Open | R32 | hard | Philipp Kohlschreiber | 6-4 3-6 7-6 6-7 8-6 |
| 2005-01-17 | Australian Open | R16 | hard | Andy Roddick | 6-3 7-6 6-1 |
| 2003-05-19 | St. Poelten | R16 | clay | Andy Roddick | 6-3 6-4 |
Averages over each player's completed matches in the selected window (151 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About