Andre Agassi, 1999 US Open

With Sampras out due to injury, Andre Agassi was the man to beat at the 1999 US Open. Agassi dropped only two sets en route to the final: to Justin Gimmelstob in the third round and Yevgeny Kafelnikov in the semifinals. In the other side of the draw Todd Martin defeated Slava Dosedel in the quarterfinals and Cédric Pioline in the semifinals to advance to his second Grand Slam final.

From Agassi’s autobiography, Open:

I’m on the verge of being number one again. This time it’s not my father’s goal or Perry’s or Brad’s, and I remind myself that it’s not mine either. It would be nice, that’s all. […]

In the final I face Martin. I thought it would be Pete. I said publicly that I wanted Pete, but he pulled out of the tournament with a bad back. So it’s Martin, who’s been there, across the net, at so many critical junctures.
At Wimbledon, in 1994, when I was still struggling to absorb Brad’s teachings, I lost to Martin in a nip-and-tuck five-setter. At the US Open the same year, Lupica [1] predicted that Martin would upend me in the semis, and I believed him, but still managed to beat Martin and win the tournament. In Stuttgart, in 1997, it was my appalling first-round loss to Martin that finally pushed Brad to the breaking point. Now it’s Martin who will be a test of my newfound maturity, who will show if the changes in me are fleeting or meaningful.

I break him in the first game. The crowd is solidly behind me. Martin doesn’t hang his head, however, doesn’t lose any poise. He makes me work for the first set, then comes out stronger in the second, taking it in a tight tiebreak. He then wins the third set – an even tighter tiebreak. He leads two sets to one, a commanding lead at this tournament. No one ever comes back from such a deficit in the final here. It hasn’t happened in twenty-six years. I see in Martin’s eyes that he’s feeling it, and waiting for me to show the old cracks in my mental armor. He’s waiting for me to crumble, to revert to that jittery, emotional Andre he’s played so often in years past. But I neither fold nor yoeld. I win the fourth set, 6-3, and in the fifth set, 6-2, and walk away knowing I’m healed, I’m back, exulting that Stefanie [2] was here to see it. I’ve made only five unforced errors in the final two sets. Not once all day have I lost my serve, and it comes as I capture my fifth slam. When I get back to Vegas I want to put five hundred on number five at a roulette table.

In the press room, one reporter asks why I think the New York crowd was pulling for me, cheering so loudly.
I wish I knew. But I take a guess: They’ve watched me grow up.
Of course fans everywhere have watched me grow up, but in New York their expectations were higher, which helped accelerate and validate my growth.
It’s the first time I’ve felt, or dared to say aloud, that I’m a grown-up.

[1] Mike Lupica, journalist
[2] Steffi Graf. They were at the beginning of their relationship.

Serena Williams, winner of the 1999 US Open

From The Bud Collins History of tennis:

The words of Richard Williams that kid sister is the more talented of the two began to ring true.

Seventh-seed Serena, 17, became the first Williams to win a major singles title, and the first black since Althea Gibson at Forest Hills in 1958 to take a major female championship. Her run to the title was not a cake walk.
In the third round, she was on the brink of defeat against 16-year-old Belgian Kim Clijsters, a future Open champion, with Clijsters leading 5-3 in the final set before Serena won 16 of last 17 points to close, 4-6 6-2 7-5.
In the round of 16, Serena rallied from a set down to top Conchita Martinez, 4-6 6-2 6-2. Facing Monica Seles in the quarters, Serena dropped the first set again before recording a 4-6 6-3 6-2 victory. Next on her agenda was defending champion Davenport. Serena took that one 6-4 1-6 6-4.

Serena had played 16 sets, but she was ready for the final against top-seeded Hingis, winner of a bruising battle over big sister Venus 6-1 4-6 6-3 the day before that shut off a prospective all-Williams final.
Hingis took too much out of herself in that strenuous showdown, and Serena was just hitting her stride. Williams led 3-6 3-5 15-40, double match point against an overwhelmed Hingis, but Martina refused to walk away. She took three games in a row and was two points from parity at one set all. Hingis led 6-5 30-0 but Serena rekindled her energy and enthusiasm and came away with a 6-3 7-6(4) victory in her first major final.

As Serena finished off Hingis, big sister Venus watched from the stands, wearing a bittersweet expression. She had been expected to win a big championship before Serena, but the following afternoon the two sisters joined forces to capture the doubles title over Chanda Rubin and Sandrine Testud 4-6 6-1 6-4.