Jan Siemerink defeated Sergi Bruguera 6-3 6-2 in the Milan round of 32 on carpet. The upset overturned the form book — Sergi Bruguera came in leading the head-to-head 3–2. Jan Siemerink narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-02-23 | London | R32 | carpet | Jan Siemerink | 6-1 7-6 |
| 1997-04-21 | Monte Carlo Masters | R32 | clay | Sergi Bruguera | 6-4 6-4 |
| 1996-08-12 | New Haven | R16 | hard | Jan Siemerink | 6-4 6-3 |
| 1994-02-07 | Milan | R16 | carpet | Sergi Bruguera | 6-4 6-4 |
| 1993-01-18 | Australian Open | R32 | hard | Sergi Bruguera | 7-6(5) 4-6 6-3 3-6 9-7 |
Averages over each player's completed matches in the selected window (199 vs 184). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About