Ryan Russell defeated Jacob Adaktusson 7-5 6-4 in the Jamaica F8 round of 16 on hard. The upset overturned the form book — Jacob Adaktusson came in leading the head-to-head 2–0. Ryan Russell claimed a first win over Jacob Adaktusson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-03 | Jamaica F13 | R32 | hard | Jacob Adaktusson | 6-2 6-3 |
| 2002-04-08 | Jamaica F1 | R32 | hard | Jacob Adaktusson | 6-0 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.