The Day 5 slate features some incredible match-ups; here's how we're betting five of our favorites.

Bernarda Pera also stayed hot by maintaining her sensational set streak with another emphatic win Wednesday.

Meanwhile, Jessica Pegula rises to a new career-high ranking of No. 7 and becomes the new American No. 1.

In a match carried over to Thursday, Félix Auger-Aliassime endured the same fate when Jason Kubler ousted Newport's No. 1 seed.

The Australian Open and French Open champion moves on to face Ričardas Berankis in the second round.

Jannik Sinner may have the trickiest opener of them all, taking on three-time Grand Slam champion Stan Wawrinka.

Peniston upset Casper Ruud to earn his first career tour-level win, and he now has a very beatable opponent in the second round.

Meanwhile, Novak Djokovic kicks off his 364th career week at No. 1—exactly seven years’ worth of weeks at No. 1.

The Norwegian is turning himself into a multi-surface threat, and adding his name to the growing list of future men’s major contenders.

A pair of first-time meetings are on tap Friday at the ATP 1000 event. Who comes through?