ST. LOUIS -- A World Series matchup between historic teams brings with it the chance to make some history. Game 5 was Adam Wainwright’s big opportunity to redeem himself for his Game 1 loss and make some. He embraced his opportunity, he was ready for it, but in the end, he lost it when the Boston Red Sox broke through to score twice in the seventh.

Afterward, the St. Louis Cardinals' ace was diplomatic: “That was a tough loss obviously, [score tied] 1-1 there in the seventh; that’s obviously the game there. Tip your hat to [Red Sox catcher David Ross], he hit a double to take the lead, and [Red Sox starter Jon Lester] did a great job. So you tip your cap to both of them.”

Adam Wainwright struck out 10 batters in seven innings, but the bottom of the Red Sox order was his undoing in the seventh. Elsa/Getty Images

You have to feel for the guy. Wainwright had to miss the 2011 season recovering from surgery and could only watch as teammate Chris Carpenter helped deal the Cards to a title with his 4-0 October run, highlighted by his Game 5 shutout of the Phillies in the National League Division Series. While Game 1’s sloppy loss was another missed opportunity, Monday night’s Game 5 against the Red Sox was Wainwright’s latest and last big chance this year to add his name to the annals of Cardinals postseason greatness as a starting pitcher, to finally have a “Carpenter game” of his own.

He felt ready for it, readying himself for it the way an ace is supposed to. “After the first game, I knew I could pitch much better than that. My delivery was horrible, and I made some great adjustments going into [Game 5],” Wainwright said. “I was very confident I was going to go out and pitch a good game.”

From the outset, this wasn’t going to be a shutout. After Dustin Pedroia’s one-out double in the first, Wainwright did the one thing Cardinals fans were afraid of: He pitched to David Ortiz instead of walking him, giving up an RBI double to Papi.

It was a decision Wainwright owned and authored, saying afterward, “I don’t like walking anybody. You got a guy on second already, it’s the first inning, and [Ortiz] hit a good pitch. He’s out-of-his-mind hot, but that was my call before the game. I said I’m not going to pitch around Ortiz, I’m going to get him out. And he hit a good pitch, and made a good swing.”

Nevertheless, through six innings Wainwright was delivering a great game, striking out the side twice and notching nine K’s, and taking a tie into the seventh, when he’d face the bottom of Boston’s order. Given how badly the bottom third of the Red Sox's lineup has hit -- with Stephen Drew struggling all postseason and opposing starter Jon Lester carrying a career-long oh-fer -- it seemed as if Wainwright would match Lester frame for frame even later into the game.

With the count 1-2, slumping Stephen Drew was able to work Wainwright for a walk that set the stage for Ross' double. Rob Carr/Getty Images

Except that he didn’t. “To be honest with you, I went out there and executed my plan all night long,” Wainwright said. “I wanted to attack them today, get them into my pitcher’s counts, keep them out of those deep counts, where they get your pitch count up early. They do a good job of that. I wanted to put them on the defensive early. I pitched them at 1-and-2 until the seventh inning.”

That’s because the seventh inning is when the narrow margin between perfect execution and success and lone mistakes leading to losses snakebit Wainwright, just as it did in Game 1. After striking out Daniel Nava, Wainwright gave up a single to rookie Xander Bogaerts and walked the stone-cold Drew, forcing him to face eighth-slot hitter David Ross instead of putting him aboard for Lester’s brand of desperation batsmanship.

What went wrong? Turning again and again to a curveball he started to miss his spots with, Wainwright struggled to execute against the weakest part of the Red Sox's order, and showed why any mistakes get punished by professional hitters.

About the curve, Wainwright observed, “It’s one of my best pitches. I had good confidence in it, and was executing it all night. Bogaerts hit a good pitch up the middle. Usually I catch that ball. I’m a little disappointed I didn’t catch that ball. But he put a good swing on it.”

Red Sox catcher David Ross touched Wainwright for two hits, including his tiebreaking ground-rule double in the seventh. Elsa/Getty Images

But Drew’s walk proved deadly. “More than anything, walking Drew there, that really hurt. That set the inning up for them. I would have liked to have attacked better there, but just didn’t make it happen,” Wainwright said. But Wainwright offered no excuses for putting Drew on first, stating, “I spun out of my delivery a couple of times, on 2-2 and 3-2, but [the ball on] 1-2 it was a good call.”

That forced Wainwright to pitch to Ross with one out and two on with the pitcher on deck, and no chance Lester would be pulled back for a pinch-hitter. Wainwright thought he had the veteran catcher set up, but even this well-laid plan went wrong for Waino.

“The pitch that Ross hit, it was the first curveball I’d thrown him in three at-bats. It’s a pitch I thought I had him set up for,” Wainwright said. “I was surprised, because I thought I had him set up for it.

"Sometimes, as painful as it is, you gotta say he did a great job. The first game I pitched against them, he hit a very good curveball with a 1-2 count over the second baseman’s head. That down-and-in curveball is a pitch that I’ve thrown all year. After you’ve thrown some hard stuff, get them to look, maybe even after a hard-ball fastball in. That bounce curveball inside looks like a heater inside and they can’t hit it.”

Instead, Ross was ready for it, belting it down the left-field line and into the stands for a ground-rule double. “This was a game of inches tonight,” Wainwright noted ruefully. “Ross’ ball was a couple inches fair, also a couple inches from staying in on the [foul] popup the pitch before. There was a lot of different things that could have happened, but didn’t.”

Just as Wainwright prepared himself to make history, he had to settle for making the wrong kind of history. It isn’t like Wainwright hasn’t been a great postseason performer this year. He beat the Pirates twice, and took a tough loss against the Dodgers. But in a World Series that has already seen players as different as Jonny Gomes and even Pete Kozma redeem themselves with their own second chances, Wainwright did not. Wainwright got his second chance to make history -- and lost it.

Christina Kahrl covers baseball for ESPN.com. You can follow her on Twitter.