8. June 10, 1997, Padres 6, Cardinals 5. Gwynn doubled in the first and scored on Ken Caminiti’s base hit. His third-inning double drove in Rickey Henderson, who had walked.
Still the Padres trailed 5-3 entering the ninth and facing Dennis Eckersley. Two singles and two outs threw the issue to Gwynn, whose double into the left-center field gap drove the two tying runs home. The Padres went on to win the game in the 12th inning. Gwynn Win Probability Added: 0.589.
7. April 30, 1993, Padres 7, Mets 6. Gwynn’s third inning single — his second of the game — led to a run, but San Diego still trailed 2-1. The Padres were down 4-1 in the fifth when Gwynn’s third hit drove in Kurt Stilwell.
The Mets led 5-3 in the seventh when Gwynn’s fourth hit — a double to right — scored Ricky Gutierrez. He same around to score the tying run on a fielding error that allowed the Padres to take a 6-5 lead. After the Mets tied the game in the top of the eighth, Gwynn’s fifth hit, an infield single, scored Darrell Sherman with the eventual winning run. Gwynn Win Probability Added: 0.591.
6. June 28, 1989, Padres 2, Dodgers 1: Dodger pitching held the Padres scoreless through seven innings of a 1-0 game at Dodger Stadium. But Benito Santiago and Tim Flannery opened the eighth with base hits off Dodger starter Mike Morgan.
Bip Roberts tried to bunt but succeeded only in forcing Santiago at third. When Marvell Wynne flied out and Roberto Alomar walked, Gwynn came to the plate against reliever Ricky Horton with the bases full and two out.
It was a make or break moment ... and Gwynn broke the Dodgers. His ground ball up the middle found a hole between second and short, scoring Wynne and Roberts with the tying and lead runs. Mark Davis held L.A. off the board through the final two innings to seal the 2-1 victory. Gwynn Win Probability Added: 0.590.
5. June 5, 1996, Padres 6, Cardinals 4. Gwynn was hitless in four at-bats entering the bottom of the ninth of a game the Cardinals led 4-2. After Jody Reed singled and Andujar Cedeno doubled him to third, Cardinal shortstop Ozzie Smith threw wildly on Chris Gwynn’s infield grounder, allowing Reed to score and narrow the margin to one run.
Cardinal manager Tony La Russa called on left-hander reliever Tony Fossas in that delicate situation, and Fossas retired the next two Padre batters without a ball leaving the infield,. That left only Gwynn, who took a strike and then launched a fly ball deep into the center field seats for a game-winning three-run home run. Gwynn Win Probability Added: 0.598.