Todor Enev defeated Boris Pashanski 6-2 6-1 in the Macedonia F2 round of 32 on clay. Todor Enev extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-07-11 | Davis Cup G2 R2: YUG vs BUL | RR | clay | Boris Pashanski | 6-2 6-4 |
| 2002-05-06 | Bulgaria 1 1 | QF | clay | Todor Enev | 0-6 6-3 6-4 |
| 2002-05-06 | Bulgaria 1 3 | R16 | clay | Boris Pashanski | 7-5 7-6(7) |
| 2001-04-23 | Bulgaria 1 | R16 | clay | Todor Enev | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.