Written By: Olivia B. Waxman

When Ashe defeated Tom Okker of the Netherlands on Sept. 9, 1968, he became the first African-American man to win a Grand Slam tennis title. The match was not only historic; it was dramatic as well. The 25-year-old Richmond, Va., native served 26 aces throughout the match, 15 of them to win the first set, which went all the way up to 14-12. (Tiebreakers were introduced in 1970.)

Even so, the record $14,000 prize money for the match went to Okker, who was the last professional player standing that year; Ashe got a $20 per diem as an amateur. But things were changing for Ashe by year’s end, he would be ranked the No. 1 tennis player by the United States Lawn Tennis Association as well as for the world around him. Fifty years later, Ashe’s win stands out as not only a milestone in tennis history, but also a milestone in the civil rights movement.

One of the many people watching tennis history be made that year was longtime TIME and LIFE photographer John G. Zimmerman, whose images from that day were included in LIFE’s cover story the following week, about Ashe’s achievement but many of Zimmerman’s pictures were never published in the magazine. The new book Crossing the Line: Arthur Ashe at the 1968 U.S. Open, from which the images above are drawn, brings together those pictures 50 years later. The book includes hundreds that have never before been seen publicly, some of which are included in the gallery above.

Zimmerman shadowed Ashe during much of the 36 hours in before, during and after the U.S. Open that year. The pictures show the surprisingly ordinary events that led up to his extraordinary achievement, such as the solitary subway ride from his hotel in Midtown Manhattan to the match in Forest Hills.

The Sept. 20, 1968, cover of LIFE magazine would describe his style of keeping it cool on the court as “icy elegance.” But he didn’t hold back at all when it came to talking about the impact of his playing within the larger fight for racial equality.

“I can make my protest heard by winning,” he told LIFE. “People don’t listen to losers.”

And win he did. By the time Ashe died in 1993, after contracting HIV from a blood transfusion following heart bypass surgery, he had won 33 singles titles and 14 doubles titles. When he was posthumously awarded the Presidential Medal of Freedom, President Bill Clinton remarked that Ashe had an “inner strength and outward dignity” that “marked his game every bit as much as that dazzling crosscourt backhand.”

Arthur Ashe hits a running forehand during his five-set victory over Tom Okker in the 1968 US Open.

Arthur Ashe hits a running forehand during his 5 set victory over Tom Okker in the 1968 US Open men’s final.

Photo by John G. ZImmerman

Crowd watches action during Men's Singles Final between Arthur Ashe and Tom Okker, U.S. Open, West Side Tennis Club, Forest Hills New York, September 9, 1968. Photo by John G. Zimmerman.

Crowd watches the U.S. Open men’s final, 1968.

Photo by John G. ZImmerman

American tennis player Arthur Ashe (1943 - 1993) playing in the US Open final against Tom Okker of the Netherlands. West Side Tennis Club, Forest Hills, New York, September 9, 1968. Photographer John G. Zimmerman

Arthur Ashe, US Open, 1968.

Photo by John G. ZImmerman

Arthur Ashe at the 1968 US Open Tennis Championships, September 9-10, 1968. Photo by John G. Zimmerman.

Ashe volleys with Okker.

Photo by John G. ZImmerman

American tennis player Arthur Ashe (1943 - 1993) playing in the US Open final against Tom Okker of the Netherlands. West Side Tennis Club, Forest Hills, New York, September 9, 1968. Photographer John G. Zimmerman

Arthur Ashe, U.S. Open, 1968.

Photo by John G. ZImmerman

American tennis player Arthur Ashe (1943 - 1993) with his father after winning the first ever US Open at the West Side Tennis Club, Forest Hills, New York, September 9, 1968. Photographer John G. Zimmerman

Ashe with his father after the win.

Photo by John G. ZImmerman

Arthur Ashe meets the press after winning the 1968 US Open Men's Tennis Championship, September 9, 1968. Photo by John G. Zimmerman.

Ashe’s post-victory press conference, 1968.

Photo by John G. ZImmerman

Arthur Ashe shakes hands with a fan in New York City, September 10, 1968, the day after winning the U.S. Open Men's Singles Championship. Photograph by John G. Zimmerman.

Ashe shakes hands with a fan in New York City, the day after winning the U.S. Open.

Photo by John G. ZImmerman

Arthus Ashe takes the New York City subway, unrecognized the day after winning the US Open Men's Singles Championship. September 10, 1968. Photo by John G. Zimmerman.

Ashe rides the New York City subway, unrecognized the day after winning the US Open.

Photo by John G. ZImmerman

Arthur Ashe and Harry Belafonte, Caesar's Palace Las Vegas, September 10, 1968. Photo by John G. Zimmerman.

Arthur Ashe and Harry Belafonte, Caesar’s Palace Las Vegas, Sept. 10, 1968.

Photo by John G. Zimmerman.

American Davis Cup team members Bob Lutz (left), Stan Smith (center) and Arthur Ashe aboard a flight to Las Vegas for Davis Cup exhibition play, September 10, 1968.  Earlier in the day, Smith and Lutz won their first Grand Slam doubles title at the US Open, defeating Davis Cup teammate Ashe and his partner, Andrés Gimeno, in the final. Photo by John G. Zimmerman.

American Davis Cup team members Bob Lutz (left), Stan Smith (center) and Ashe aboard a flight to Las Vegas for Davis Cup exhibition play, September 10, 1968. Earlier in the day, Smith and Lutz won their first Grand Slam doubles title at the US Open, defeating Davis Cup teammate Ashe and his partner, Andrés Gimeno, in the final.

Photo by John G. Zimmerman.

Arthur Ashe in the men's locker room, West Side Tennis Club, Forest Hills, New York, September 10, 1968. Photo by John G. Zimmmerman.

Ashe in the men’s locker room, West Side Tennis Club, Forest Hills, N.Y.

Photo by John G. ZImmerman

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