Pillsbury negotiated the final terms of the first Anglo-American cable match with Sir George Newnes, president of the London Chess Club. Sir George donated the Newnes Cup, held by the winning team each year until the next match. Pillsbury played on the first board for the US team in the first eight cable matches (+1 -2 =5). Pillsbury also helped prepare the US House of Representatives team for their 1897 cable match against the House of Commons.

Pillsbury was considered the strongest player in the US. He played two matches for the US championship against Showalter, winning both of the Pillsbury - Showalter (1897) (+10-8=3) and Pillsbury - Showalter (1898) (+7-3=2) matches. However Pillsbury was not especially eager to be named US champion: “I was not seeking the match, and even if I should win I shall leave Showalter in possession of the title; I am not in search of any title but one.” The “one” title was, of course, World Champion. Pillsbury wrote to New York following his success at Hastings that there had been some talk of arranging a title match with Lasker, but, as with so many proposed world championship matches over the years, nothing came of it. Pillsbury's inability to obtain a title match against Lasker was most likely due to Pillsbury's failure to secure enough financial backing to induce Lakser to agree to a match.

Pillsbury was accomplished at blindfold chess and often playing mutiple games blindfolded in his exhibitions. He set an early world record for number of simultaneous blindfold games, playing 20 games in 1900 in Philadelphia. He was also a skilled checkers player, and would sometimes include checkers and whist games in his exhibitions. Pillsbury's exhibitions were quite impressive for the day. Jose Raul Capablanca wrote: “The effect of Pillsbury's displays was immediate. They electrified me, and with the consent of my parents I began to visit the Havana Chess Club.”

Pillsbury played a number of consultation games over the years. Such games were sometimes played on off days of tournaments between players with no adjourned games. Pillsbury played with or against masters such as Henry Edward Bird, Blackburne, Chigorin, David Janowski, Lasker, William Ewart Napier, Georg Marco, Frank James Marshall, Carl Schlechter, Showalter, Tarrasch, Teichmann, and others.

While there is general agreement that Pillsbury died of syphilis, when he contracted the disease is debatable. Syphilis shows great variability in its time course across patients and can easily mimic symptoms of other diseases, so a definitive answer is unlikely. Pillsbury was ill during the second half of the St. Petersburg tournament, which was attributed to influenza at the time. He was also quite ill during the Nuremberg tournament, and, of course, during Cambridge Springs. He suffered two strokes during the last year and a half of his life.

Pillsbury wrote no chess books. He wrote occasional newspaper reports on tournaments and matches and wrote a column for the Philadelphia Inquirer. Although there are few known correspondence games played by Pillsbury, one of the early correspondence chess organizations in the US was named in his honor (Pillsbury National Correspondence Chess Association).