Tim Henman defeated Juan Ignacio Chela 6-2 6-7 6-4 in the Monte Carlo Masters round of 16 on clay. The upset overturned the form book — Juan Ignacio Chela came in leading the head-to-head 5–3. Tim Henman narrowed the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-13 | Cincinnati Masters | R64 | hard | Juan Ignacio Chela | 6-4 3-6 6-3 |
| 2005-08-15 | Cincinnati Masters | R32 | hard | Juan Ignacio Chela | 6-4 6-4 |
| 2005-05-09 | Hamburg Masters | R16 | clay | Juan Ignacio Chela | 3-6 6-4 6-2 |
| 2005-03-21 | Miami Masters | R32 | hard | Tim Henman | 6-3 6-1 |
| 2004-05-24 | Roland Garros | QF | clay | Tim Henman | 6-2 6-4 6-4 |
| 2004-01-05 | Doha | R16 | hard | Tim Henman | 6-3 6-4 |
| 2002-08-26 | US Open | R32 | hard | Juan Ignacio Chela | 6-3 6-3 6-2 |
| 2000-04-17 | Monte Carlo Masters | R32 | clay | Juan Ignacio Chela | 6-2 4-6 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.