1–ranked woman player Margaret Smith Court, which he won, and another against the then-current women's champion Billie Jean King,[6] which he lost.

[7][8] The latter, the primetime "Battle of the Sexes" match, remains one of the most famous tennis events of all time, with a $100,000 ($686,000 today) winner-takes-all prize.

With the help of Bartosh and others, Riggs played in various National Tournaments and by the time he was 16 was the fifth-ranked junior player in the United States.

[11] In August aged 16, Riggs won the Ohio Valley tournament beating Archie McCallum in the final.

"[12] In July Riggs won the Utah championships in Salt Lake City beating Joe Hunt in the final.

"The largest crowd in Salt Lake tennis history watched the final day’s encounters which climaxed the greatest tournament ever staged in this state".

Riggs won the U.S. Men's Clay Court Championships in Chicago, beating Frank Parker in the finals with drop shots and lobs.

"Riggs, who has a well-rounded game and a rare knack of keeping the ball in play, owed his victory to his accurate backhand returns to the far corners.

Riggs won the eighth and last game easily and a match which while rather lacking pep, had been entertaining enough in its clever way.

Riggs won 14 tournaments in 1940 at Palm Beach, Pensacola, Miami, Augusta, U.S. Indoors, River Oaks in Houston, the Cincinnati Open, Fox River Valley in Neenah, Western championships in Indianapolis, Seabright, Eastern grass court championships, Pacific southwest, Pacific Coast and New Orleans.

When the marathon ended with darkness settling over the court, a sell-out gallery stood and cheered while Bobby received the famous Seabright bowl.

[27] During his military service, Riggs was a cornerstone member of the 1945 league champion 14th Naval District Navy Yard Tennis Team.

He was granted a five-minute rest while his muscle was soothed but when play was resumed, Riggs continued his precise devastating base-line attack and broke the Oakland redhead's service for a 5-2 advantage.

After a 10-minute intermission, during which time Budge's arm apparently failed to respond to treatments, they returned to the court for the formality of concluding the match.

Riggs also won events at Palm Springs, Phoenix, Pasadena, Chattanooga, Boston, Oyster Harbors, Wentworth-by-the-Sea, Jefferson, Pittsburgh, Indianapolis, Oklahoma City and U.S.

[33] Budge had sustained an injury to his right shoulder in a military training exercise during the war and had never fully recovered his earlier flexibility.

He also told Riggs and Budge that the winner of the Professional American Singles Championship, to be held at Forest Hills, would establish the World Champion who would defend his title against Kramer.

Harris then signed Pancho Segura and Dinny Pails at $300 ($4,090 today) per week to play the opening match of the Riggs–Kramer tour.

By that point, however, Kramer had stepped up his second serve to take advantage of the fast indoor courts they played on and was now able to keep Riggs from advancing to the net.

The final score was 69 victories for Kramer versus 20 for Riggs, the last time an amateur champion had beaten the reigning professional king on their first tour.

Small in stature, he lacked the overall power of his larger competitors such as Budge and Kramer, but made up for it with brains, ball control, and speed.

In his autobiography, Riggs wrote, "In the 1946 match with Budge [for the United States Pro Championship], I charged the net at every opportunity.

After many failed attempts to lure Billie Jean King, he challenged Margaret Court, 30 years old and the top female player in the world, and they played on May 13, Mother's Day, in Ramona, California.

Riggs used his drop shots and lobs to keep Court off balance;[43][44] his easy 6–2, 6–1 victory in less than an hour landed him on the cover of both Sports Illustrated and Time magazine.

Following Court's loss to Riggs, King decided to accept his challenge,[47][48] and the two met in the Houston Astrodome on prime-time television on Thursday, September 20, in a match billed as The Battle of the Sexes.

[6] The oddsmakers and writers favored Riggs;[49] he built an early lead, but King won in straight sets (6–4, 6–3, 6–3) for the $100,000 winner-take-all prize.

[7][8] The ESPN program Outside the Lines[50] made an allegation that Riggs took advantage of the overwhelming odds against King and threw the match to get his debts to the mob erased.

The program featured a man who had been silent for 40 years, for reasons of self-protection, who claimed that he had worked at a country club, and there heard several members of the mafia talking about Riggs throwing the match in exchange for cancelling his gambling debt to the mob.

In the 2017 film adaptation Battle of the Sexes, Riggs was played by Steve Carell, with Emma Stone as Billie Jean King.

He and Lornie Kuhle founded the Bobby Riggs Tennis Club and Museum in Encinitas, California to increase awareness of the disease and house his memoirs/trophies.