Benjamin Ugarte defeated David Fleming 3-6 6-2 7-5 in the Chile F4 round of 32 on clay. Benjamin Ugarte extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-08-19 | Ecuador F2 | R32 | hard | Benjamin Ugarte | 7-5 7-5 |
| 2011-10-31 | Chile F11 | R32 | clay | David Fleming | 7-6(3) 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.