Perry-Smith, the father, was an athlete who demonstrated prowess in rowing, boxing and skiing. He was a member of the First City Troop of Philadelphia and when the Spanish-American War broke out he was commissioned as a captain in the Commissary of Subsistence (Supply Corps) in Fitzhugh Lee's 7th Army Corps.
He died in 1899 at the age of 38 of nephritis while aboard the USS Missouri which was anchored in Havana. His widow remarried and moved to Germany. His son later returned to the US and lived off his trust fund.
Chessplaying Perry-Smith played in all of the Franklin Chess Club Championships that were played between 1893 and 1898 and in several rapid tournaments. According to the Philadelphia Ledger of May 1898 Perry-Smith played in a continuous tournament of the Mercantile Library Cup and received a prize for the most wins. The paper added that there was no prize for the most losses or Perry-Smith would have received that one, too.
Our Folder, a monthly magazine published in Philadelphia by the Good Companion Chess Problem Club, had an article describing a dinner in 1923 that had a table decoration, the Oliver Perry-Smith silver plate, upon which was engraved the final position of his win against the Turkish Ambassador. A big deal was made of that game, but the Ambassador played horrible chess and allowed Perry-Smith to mate in 7 moves. The game is included in the score of his game against Kemeny below. According to the Edo rating site his rating was between about 1900-2000 in the 1890's.