Tour singles titles: Montreal 1997 and Newport 1999
29
Career-high singles ranking, August 1997
1,342
His ranking after a year out with a knee injury
1993
NCAA singles champion for Tennessee
QF
Australian Open 2000, his best major result
Playing career
Woodruff grew up in Knoxville, Tennessee, and won the NCAA singles title for the University of Tennessee in 1993 before turning professional. In August 1997, unseeded and ranked No. 57, he won the Canadian Open in Montreal, beating Goran Ivanišević, Mark Philippoussis, Yevgeny Kafelnikov and, in the final, the French Open champion Gustavo Kuerten 7-5, 4-6, 6-3. The title took him to a career-high No. 29. In December 1997 he hurt his knee, needed surgery and a year of rehabilitation, and fell to No. 1,342.
His return in 1999 was the biggest climb on the tour that year: a semi-final at Indian Wells, the Newport title on grass and a year-end ranking of No. 51. At the 2000 Australian Open he beat the 11th seed Tim Henman in five sets and reached the quarter-finals, where Pete Sampras beat him. A few weeks later, called into the Davis Cup team, he beat Wayne Black 6-3, 6-7, 6-2, 6-4 in Harare as the United States came from 2-1 down to beat Zimbabwe 3-2. He retired in 2001, returned to Tennessee as a volunteer assistant coach in 2002 and became head coach in 2017. He entered the Tennessee Sports Hall of Fame in 2025.
On grass
Newport 1999 final
Beat Kenneth Carlsen 6-7, 6-4, 6-4. He broke for 5-4 in the second set, led 4-0 and 5-1 in the third and held at 5-4 after Carlsen won three games in a row. It was his first title in almost two years and lifted him from No. 116 to about No. 90
Newport 1999 run
Beat Rogier Wassen 6-3, 6-2, David Prinosil 6-2, 6-4, Stefano Pescosolido 6-2, 6-4 and Wayne Arthurs 7-6, 6-7, 6-4 before the final
Newport 1999 doubles
Runner-up with Sargis Sargsian to Wayne Arthurs and Leander Paes 6-7, 7-6, 6-3
Leading grass titles only: the grass majors, tour-level grass events since 1968 and the leading grass championships before 1968. †single source; ‡ sources disagree. Roll of champions
"I came here with no expectations, so winning was a great feeling"
Anecdotes
The person behind the player.
Knoxville, 1993
A hometown champion
A Knoxville native, Woodruff stayed at home for college and won the NCAA singles title for Tennessee in 1993. He later returned to coach the Vols, first as a volunteer assistant, and the Tennessee Sports Hall of Fame inducted him in 2025.
Unseeded, he saved a match point in his opening match and then beat five more seeds to win the Canadian Open, hitting 18 aces in the final against Gustavo Kuerten. "I've really been working on my serve, hitting lots of bucketfuls of balls at home and it's really paid off at this tournament," he said.
Woodruff hurt his knee while kicking field goals on an American football field with fellow pro Richey Reneberg. Surgery and a year of rehabilitation followed, and his ranking fell from around 30 to No. 1,342.
After beating Tim Henman 7-5 in the fifth set to reach the quarter-finals, Woodruff apologised for his fist-pumping: "I am not a rah-rah kind of in-your-face guy," he said. "Obviously I couldn't control it."
With Pete Sampras and Todd Martin out, Woodruff joined Andre Agassi for the Davis Cup tie in Zimbabwe. He beat Wayne Black in four sets, finishing with his 15th ace, as the United States recovered from 2-1 down to win 3-2.