The Matchup:

This Matchup was practically penciled in when the bracket came out. In the first round, Reggie Jackson beat ASU basketball legend Joe Caldwell with 88 percent of the vote. A few days later, Darren Woodson secured his spot in the Sweet 16 with 87 percent of the vote over Paul Lo Duca.

Career-Defining Moment:

For Jackson, this one’s easy. It was that night in 1977 where he came to the park as Reggie Jackson and left as “Mr. October.” In Game 6 of the ‘77 World Series, Jackson etched his name into the Fall Classic lure, belting three home runs over the Yankee Stadium wall on just three pitches from three different Los Angeles Dodgers’ pitchers. That night, Jackson won his fourth out what would be five World Series in his 21-season Hall of Fame career.

Woodson’s signature moment is a little tougher to pick out as he won three Super Bowls with the Dallas Cowboys, including recovering a fumble in the 1994 Super Bowl against the Bills. In 2002, however, his illustrious time with America’s Team reached the record books as he became the Cowboys all-time leading tackler. It seems right that we put that on here because it was overshadowed when it occurred — that’ll happen, though, when your teammate Emmitt Smith breaks the NFL career rushing record the same game.

Where are they now?

Just a few months ago, the Yankees named three former players — Alex Rodriguez, Hideki Matsui and Jackson — as a special advisors to the organization. On the side, Jackson has amassed a great collection of cars. He had so many, too, that he had to auction off some of them because he ran out of space.

After his playing career, Woodson joined ESPN as a NFL analyst for mainly SportsCenter and NFL Live, where he was co-workers with ASU head coach Herm Edwards. He is still involved in the Dallas community, serving as a board member for the North Texas branch of the Make-a-Wish Foundation.

Resumes: