Andrei Medvedev defeated Tim Henman 6-2 6-3 in the Estoril quarter-final on clay. The result followed the form book — Andrei Medvedev came in defending last year's round of 16. Andrei Medvedev extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Basel | R16 | hard | Tim Henman | 5-7 6-4 6-1 |
| 1998-04-03 | Davis Cup G1 QF: GBR vs UKR | RR | carpet | Tim Henman | 6-2 6-7(4) 6-4 1-6 6-1 |
| 1997-08-04 | Cincinnati Masters | R64 | hard | Andrei Medvedev | 6-3 6-3 |
| 1997-07-11 | Davis Cup G1 PO: UKR vs GBR | RR | clay | Andrei Medvedev | 6-7(5) 6-3 6-4 6-4 |
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 (60 vs 200). ATP, WTA & Challenger.