Leandro Migani defeated Juan Sebastian Cabal 7-6 6-4 in the Chile F6 semi-final on clay. The upset overturned the form book — Juan Sebastian Cabal came in leading the head-to-head 1–0. Leandro Migani claimed a first win over Juan Sebastian Cabal in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-01 | Italy F13 | QF | clay | Juan Sebastian Cabal | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.