In 1996, the Padres finished with a 91–71 record winning the National League West, earning Bochy NL Manager of the Year honors.

Key players such as Tony Gwynn (who was a part of the team's 1984-pennant winning season), Greg Vaughn, and pitchers Andy Ashby, Trevor Hoffman (who saved 53 games that season and was a runner-up in Cy Young Award voting), and Kevin Brown all contributed heavily to San Diego's success in 1998.

The Padres defeated the Braves in the NLCS 4 games to 2, winning the franchise's second pennant en route to the World Series.

During the 1997–98 offseason, the Yankees made multiple moves, most notably trading for Scott Brosius from the Oakland Athletics, Chuck Knoblauch from the Minnesota Twins, and purchasing the contract of Alfonso Soriano from Nippon Professional Baseball.

The team's "Core Four" of pitcher Andy Pettitte, shortstop Derek Jeter, catcher Jorge Posada, and closer Mariano Rivera, alongside other stars like pitchers David Cone and ace David Wells, and outfielders Paul O'Neill and Bernie Williams helped the Yankees reach new heights in 1998.

In Game 1, Kevin Brown took the hill for the Padres while the Yankees sent ALCS MVP David Wells to start.

The Yankees began the scoring in the second inning, when rookie Ricky Ledee laced a two-run double into the right field corner with the bases loaded.

However, the Padres battered Wells hard, beginning in the third inning when Greg Vaughn homered to right-center with a man aboard tying the game up at two runs apiece.

Trailing 5–2, Jorge Posada singled and Ledee walked with one out in the seventh for the Yankees, ending the night for Brown.

After Derek Jeter singled, Mark Langston relieved Wall and after Paul O'Neill flied out, walked two to load the bases.

Chuck Knoblauch walked to lead off the first, stole second, and scored on third basemen Ken Caminiti's throwing error to first on Paul O'Neill's ground ball.

After Bernie Williams grounded out, RBI singles by Chili Davis and Scott Brosius gave the Yankees a 3–0 lead.

Gomez scored on Quilvio Veras's double to put the Padres on the board, but in the bottom of the inning, Jorge Posada's two-run home run off of Brian Boehringer extended the Yankees' lead to 9–1.

Gwynn then scored on Ken Caminiti's sacrifice fly to the warning track to give San Diego a 3–0 lead.

However, Hoffman blew the save when he walked Tino Martinez before Scott Brosius tagged a three-run blast over the fence in dead center.

Rivera allowed a single to Gwynn and a deep sacrifice fly to Greg Vaughn to cut the lead to 5–4, but Caminiti struck out to end the inning.

Andy Pettitte, who struggled throughout the regular season and had turned in a poor start in the ALCS, outdueled Kevin Brown in Game 4, throwing 7+1⁄3 shutout innings.

After Ken Caminiti reached with a single to load the bases, Rivera was able to get Jim Leyritz, known for his clutch postseason home runs, to fly out to end the threat.

[7][6] On October 11, 2005, A&E Home Video released The New York Yankees Fall Classic Collectors Edition (1996–2001) DVD set.

The loss made the Padres the first expansion team to lose two World Series, having lost in 1984 to the Detroit Tigers.

Bochy, however, would go on to win three World Series titles as manager of the San Francisco Giants in 2010, 2012, and 2014 and then the Texas Rangers in 2023.