Five American men are through to the round of 16 at Indian Wells for the first time since 2004

Ben Shelton showed his fighting spirit at Indian Wells on Monday, rallying from 5-3 down in the second set for a 6-3, 7-5 win over Karen Khachanov.

And it was much more than just any third-round win.

With Taylor Fritz, Tommy Paul, Brandon Nakashima and Marcos Giron having already won their third-round matches, Shelton’s victory also ensured that there would be five American men through to the round of 16 at Indian Wells for the first time in 21—yes, 21— years.

The last time that happened was in 2004, when the five American men were Andre Agassi, Andy Roddick, James Blake, Mardy Fish and Taylor Dent.

Three of that quintet (Agassi, Roddick and Blake) would make it to the quarterfinals, with one of them (Agassi) reaching the semifinals.

Roger Federer beat Tim Henman for the title that year.

Paul and Giron were the first two of the five to advance to the round of 16, winning their third-round matches on Sunday—Paul, the No. 10 seed here, snapped a three-match losing streak against 2021 Indian Wells champion Cam Norrie with a 6-3, 7-5 victory, while Giron, who’s unseeded, took out his second straight seed, edging No. 26 seed Alexei Popyrin, 5-7, 6-3, 6-3.

Giron had upset the No. 4 seed, Casper Ruud, in the second round.

Fritz, Nakashima and Shelton all won their third-round matches on Monday, starting with Fritz, who dropped the first set but then cruised against Alejandro Tabilo, 4-6, 6-3, 6-1. Nakashima then beat Matteo Arnaldi, 6-2, 6-4, followed by Shelton’s aforementioned victory over Khachanov.

Fritz, Shelton and Nakashima are the No. 3, No. 11 and No. 32 seeds here.

With Shelton and Nakashima playing each other next, there’s guaranteed to be at least one American man into the quarterfinals, with up to four if the other three all win their respective fourth-round matches.

Paul and Giron will be the first of the five to play their fourth-round matches on Tuesday. They’re both scheduled on Stadium 1, starting with Giron, who’ll face No. 20 seed Arthur Fils in the last match of the day session.

They’ll be playing each other for the first time.

Paul will face No. 5 seed Daniil Medvedev in the first match of the night session. Medvedev leads that head-to-head, 3-1, including a 1-6, 7-6 (3), 6-2 victory for the Russian in the semifinals here a year ago—but Paul did win their only meeting since then, 6-1, 6-4, on clay, in the fourth round of Rome.

Fritz, Shelton and Nakashima will all play next on Wednesday.