Donald Young defeated Kevin Anderson 3-6 7-6 6-2 in the Washington quarter-final on hard. The upset overturned the form book — Kevin Anderson came in leading the head-to-head 5–1, defending last year's quarter-final. Donald Young narrowed the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-10-29 | Basel | R16 | hard | Donald Young | 6-2 7-6(6) |
| 2015-02-14 | Memphis | SF | hard | Kevin Anderson | 4-6 6-3 6-4 |
| 2011-06-08 | London | R32 | carpet | Kevin Anderson | 6-2 6-4 |
| 2011-02-22 | Delray Beach | R32 | hard | Kevin Anderson | 6-7(5) 7-6(4) 6-2 |
| 2010-04-06 | Houston | R32 | clay | Kevin Anderson | 7-5 6-3 |
| 2010-02-14 | Memphis | QF | hard | Kevin Anderson | 6-4 6-7(5) 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.