San Diego Padres history: The 10 best games of Tony Gwynn's career

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.

4., June 6, 1984, Padres 7, Giants 6. The Padres trailed Atlanta by half a game entering the second half of a Sunday doubleheader at Candlestick. San Diego won the first game 7-5, but trailed this one 6-4 entering the ninth inning.

Hitless to that point and due up seventh, Gwynn was unlikely to get a chance to influence the outcome. But Carmelo Martinez and Garry Templeton both singled off Giants reliever Gary Lavelle, and Bruce Bochy’s fly ball got one run home to make the score 6-5. Steve Garvey followed with a hit, but Templeton was thrown out at home attempting to score the tying run.

Alan Wiggins kept the inning alive with a hit and Bobby Brown worked a walk, giving Gwynn his chance. He lined a single off Lavelle that scored both Garvey and Wiggins with the tying and go-ahead runs. When Rich Gossage stopped the Giants in the bottom of the ninth, San Diego had a comeback 7-6 victory. Gwynn Win Probability Added: 0.636.

3. July 20, 1984, Padres 3, Pirates. Not surprisingly, 1984 – with three entries – is the most represented of Gwynn’s seasons on this list.  By mid-July, the Padres commanded the NL West race, holding a six and one-half game lead on the Braves. But they lost the first game of this Friday night doubleheader at Three Rivers, and were being shut out by John Tudor entering the eighth inning of the second game.

With first and sixth inning hits, Gwynn was the only Padre experiencing any success against Tudor. Down to their final five outs, Bruce Bochy beat out a base hit and, one out later, Alan Wiggins also singled, moving pinch runner Kurt Bevacqua to second.

Power was only an occasional aspect of Gwynn’s game but, against Tudor, he muscled up and rocketed a home run into the right field seats. It was all the offense San Diego would generate in the game, and it was enough to seal an eventual 3-2 victory. Gwynn Win Probability Added: 0.697.

2. June 11, 1993, Padres 5, Dodgers 4. The situation looked hopeless for the home team on this Friday evening at Jack Murphy Stadium. The Dodgers had steadily built a 4-0 lead which Kevin Gross protected, holding the Padres to just three hits over eight innings.

But when Gross was lifted for a pinch hitter in the bottom of the eighth, the Padres got into the Dodger bullpen, and the gettings were good. After Gary Sheffield touched a young Pedro Martinez for a single, Fred McGriff homered to make the score 4-2. A walk, two singles, and two strikeouts later, Gwynn came up against left-handed Omar Daal, the third Dodger pitcher of the inning. 

Gwynn took a first pitch ball, then lined Daal’s second pitch into the gap in center. Derek Bell and Craig Shipley scored easily and, when Ricky Gutierrez beat the relay home, Gwynn’s hit had completed a stunning five-run rally good for a walkoff victory. Gwynn Win Probability Added: 0.749. 

1. June 21, 1986, Padres 8, Dodgers 7. From an impact standpoint, Gwynn’s greatest single regular-season game unfolded under the Dodger Stadium lights. His team was in a 5-0 hole when Gwynn went to work in the seventh inning with a ground single into left field that scored Garry Templeton and advanced two other runners.  Those runners both later scored on a Steve Garvey single.

The Padres still trailed 6-5 when Gwynn led off the ninth against Ken Howell. He singled, stole second, took third on an Alex Trevino throwing error, and scored the tying run on a Kevin McReynolds fly ball.

Fast-forward to the 11th for a repeat: A Gwynn single, a steal of second and a lead run scored on McReynolds’ double. The only problem was that the Dodgers tied the game in the bottom of the 11th.

And so things proceeded into the 14th inning. After Tim Flannery opened with a hit, Gwynn beat out an infield grounder, moving the lead run into scoring position. Two strikeouts later, John Kruk singled to score Flannery. This time the Padre pen held, producing an 8-7 victory. Gwynn Win Probability Added: 0.757.

San Diego Padres: Tony Gwynn’s five best postseason games

5. Game 2, NLDS, Oct. 3,  1996, Padres 4, Cardinals 5. Gwynn’s sixth-inning single scored two runs and pulled the Padres within one run of the lead. The Cardinals would hang on for the victory and sweep the series. Gwynn Win Probability Added: 0.148.

4. Game 1, NLCS, Oct. 7, 1998, Padres 3, Braves 2. Gwynn’s fifth-inning single off John Smoltz drove in the tying run. San Diego would win on a 10th-inning Ken Caminiti home run. Gwynn Win Probability Added: 0.219.

3. Game 3, World Series, Oct. 20, 1998, Padres 4, Yankees 5. This was San Diego’s best hope of averting a sweep at the hands of one of the all-time greatest teams. Gwynn’s sixth-inning single drove in two runs and put the Padres ahead 2-0. Moments later, he scored the inning’s third run. He singled again in the eighth, setting up a fourth run that pulled the Padres within a run at 5-4. Gwynn Win Probability Added: 0.259.

2. Game 1, World Series, Oct. 17, 1998, Padres 6, Yankees 9. Gwynn’s second of three hits that night was a fifth-inning home run that scored Quilvio Veras ahead of him and gave San Diego a 4-2 lead. His eighth-inning single eventually led to a run but, by that time, the Yanks were too far out front. Gwynn Win Probability Added: 0.301. 

1. Game 5, NLCS, Oct. 7, 1984, Padres 6, Cubs 3. Gwynn starred in what may rank as the greatest game in Padres history.  With the Cubs leading 3-0 and Rick Sutcliffe seemingly in complete command of the decisive NLCS game, Gwynn’s sixth-inning single touched off a two-run rally.

One inning later, Gwynn’s double to center scored Tim Flannery and Alan Wiggins and turned a 3-3 tie into a 5-3 Padres edge. One batter later, Steve Garvey’s hit scored Gwynn with an insurance run as the Padres reached the World Series for the first time in franchise history. Gwynn Win Probability Added: 0.323.