| Score: | 1–6, 4–6, 6–3, 6–3, 6–3 |
| Draw: | 37 |
| Seeds: | – |
See main article: 1899 Wimbledon Championships. Arthur Gore defeated Sydney Smith 3–6, 6–1, 6–2, 6–4 in the All Comers' Final, but the reigning champion Reginald Doherty defeated Gore 1–6, 4–6, 6–3, 6–3, 6–3 in the challenge round to win the gentlemen's singles tennis title at the 1899 Wimbledon Championships.[1] [2]