I was reading my pal Marcus's great cardblog All The Way To The Backstop, as I tend to do just about every day, when I noticed an offhand remark he made in his most recent post, in which he wondered how many times Tony Gwynn homered and struck out in the same game. That got me wondering as well, and since I'm the type to really dwell on something once it gets in my mind, I used Baseball-Reference's Play Index to look up how many times it happened. There were 13 such occasions. I kept poking around, and pored over the box scores and play-by-play from each game to get the names of the pitchers involved and whatever other useful information I could glean. Below is a table of every time Tony Gwynn homered and struck out in the same game; below that are additional related facts.
| Date | HR Pitcher | K Pitcher |
| 04/28/85 | Fernando Valenzuela | Valenzuela |
| 04/13/86 | Tom Browning | Browning |
| 05/23/86 | Jesse Orosco | Sid Fernandez |
| 08/13/86 | Doyle Alexander | Alexander |
| 09/17/86 | Vida Blue | Mark Davis |
| 07/05/87 | Bryn Smith | Jeff Parrett |
| 04/11/89 | John Smoltz | Jose Alvarez |
| 07/12/90 | John Smiley | Bill Landrum |
| 07/11/93 | Kent Bottenfield | Pete Young |
| 06/19/94 | Brian Williams | Williams/ Ross Powell |
| 07/29/97 | Tyler Greene | Ricky Botallico |
| 04/15/99 | Brian Bohanon | Bohanon |
| 05/23/00 | Al Leiter | Leiter |
- Gwynn added a walk in the 1990 and '97 games for his only two games featuring all three true outcomes; worth noting is that in the 1990 game, his strikeout came in the tenth inning, and he walked in the thirteenth. For contrast, Jim Thome has the most career three-true-outcomes games with 154; Mark McGwire is second with 133, and Babe Ruth, Barry Bonds, and Adam Dunn are tied for third with 125.
- Tony struck out and homered in the same game most frequently in April and July, four times in each. The only other month he did it twice in was May; he did it on May 23 twice, 14 years apart.
- Only six pitchers allowed a homer to and struck out Tony Gwynn in the same game: Fernando Valenzuela, Tom Browning, Doyle Alexander, future teammate Brian Williams, Brian Bohanon, and Al Leiter.
- The 13 games were split 7-6 home versus road, and the Padres record in these games was 7-6.
- Of the 13 home runs, four took place in the first inning, followed by two each in the fifth, sixth, and ninth. The other three came in the fourth, seventh, and eighth.
- The first inning also holds the strikeout lead, with five. He struck out in three separate ninth innings, followed by the third and seventh with a pair apiece.
- Gwynn homered in the first and struck out in the ninth two different times, and did the complete opposite twice also. He homered in the fifth and struck out in the seventh twice, as well.