Boasting home-field advantage, it would be easy to argue that Lester and the Red Sox would have a clear-cut advantage in the series opener.
Yet Wainwright and the Cardinals can count on a few advantages of their own, and those may be enough to give St. Louis' ace the edge at the outset.
With both Boston and St. Louis employing stellar bullpens, it is safe to say that scoring early will be essential to each team's prospects for victory.
It is worth noting that Wainwright has never faced the Red Sox in the regular season, but we can evaluate some of the factors that he can count on.
Wainwright is entering the World Series on a hot streak—boasting a 1.80 ERA and 0.943 WHIP in his last five starts. He has been an essential element to the Cardinals' success this postseason and hopes that trend can continue.
Where Lester could find trouble, however, is facing off against St. Louis' right-handed and switch-hitting batters.
Left-handed batters are hitting only .237 against him this season, but righties are batting .257. Power numbers also jump up—13 home runs from the right side compared to only six from the left side of the plate.
Look for Cardinals sluggers Matt Holliday and Carlos Beltran to try and do some damage here.
Another facet that bodes well for St. Louis is the fact that the Red Sox struggled against the right-handed rotation of the Detroit Tigers in the ALCS.
Detroit's starters held Boston's hitters to a .189/.275/.287 batting line with a postseason series-record 55 strikeouts.
The Red Sox did most of their damage against the Tigers' bullpen—something that will not be as easy against the Cardinals.
Assuming that St. Louis can give Wainwright at least three runs of support, the Cardinals ace becomes even more dominant.
Over his career, Wainwright owns a career 2.90 ERA when his team scores three to five runs in support.
On the other hand, Lester's ERA jumps up to 4.19 this season when the Red Sox score the same amount of runs in support.
As argued by Matt Snyder of CBS Sports, Wainwright is the better pitcher overall, especially when those statistics are factored into the equation.
While Wainwright has an edge over Lester in Game 1, Wainwright still has to put that advantage into practice. He must be able to pitch effectively against Boston's vaunted lineup and count on getting just enough run support to ensure he can maintain the lead.
If that happens, the Cardinals can turn the game over to their talented bullpen, which has done the job thus far in the postseason.
That sounds like a good formula, one Wainwright and St. Louis can count upon to take a 1-0 lead in the series.
All statistics, records and accolades courtesy of Baseball-Reference.com unless otherwise indicated.
Peter Panacy is a featured columnist for Bleacher Report. Follow him @PeterMcShots on Twitter.