

Casper Ruud advanced when Matteo Berrettini retired 7-5 2-0 in the Rome Masters round of 32. Casper Ruud extended the head-to-head to 6–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-09-24 | Tokyo | R16 | hard | Casper Ruud | 7-6 6-2 |
| 2023-01-02 | United Cup | RR | hard | Matteo Berrettini | 6-4 6-4 |
| 2022-08-29 | US Open | QF | hard | Casper Ruud | 6-1 6-4 7-6 |
| 2022-07-18 | Gstaad | F | clay | Casper Ruud | 4-6 7-6 6-2 |
| 2021-05-03 | Madrid Masters | SF | clay | Matteo Berrettini | 6-4 6-4 |
| 2020-09-14 | Rome Masters | QF | clay | Casper Ruud | 4-6 6-3 7-6 |
| 2020-08-31 | US Open | R32 | hard | Matteo Berrettini | 6-4 6-4 6-2 |
| 2019-05-27 | Roland Garros | R64 | clay | Casper Ruud | 6-4 7-5 6-3 |
Averages over each player's completed matches in the selected window (81 vs 64). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Ruud C.: 4 days rest · 1 match, 15 games (7d) · Berrettini M.: 5 days rest · 2 matches, 58 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the clay field, opponent-adjusted over 52 weeks). About