Starting this Friday night, the Red Sox face their most challenging opponent since the tumultuous 7/31 trading deadline, as they march into Chicago’s South Side to take on Crazy Ozzie Guillen’s Pale Hose in a 4 game series.

This is the first time these teams have faced off in 2008, and the most meaningful series they’ve had in quite a while. How do these two squads match up? Let’s break it down position-by-position.

Starter, Game 1
BOS: Jon Lester
CHI: Mark Buehrle

Buehrle (a.k.a. Supreme Eater of Innings) is coming off of rough start against Kansas City. His fastball is hovering around the 84-88 MPH range right now, and he may be finally showing signs of fatigue from throwing nearly 1,800 innings before his 30th birthday. Lester has been rolling since late April, and looks to continue his outstanding season powered by his improvement in command and a revamped cut fastball.

Advantage: Boston

Starter, Game 2
BOS: Daisuke Matsuzaka
CHI: Jose Contreras

In Dice-K’s last start against Oakland, he went back to basics. We’ve all hears about his legendary pitch arsenal, and how Jason Varitek quipped that he needed all 10 fingers to call Matsuzaka. Well, 88% of his 103 pitches against the A’s were either fastballs or sliders. And it worked out wonderfully, leading to 8 strikeouts and only 2 walks. Admittedly, he might have to change his approach against the much tougher Chicago lineup.

Advantage: Boston

Starter, Game 3
BOS: Clay Buchholz
CHI: Gavin Floyd

A few days ago, I mentioned that Clay Buchholz was suffering from both bad luck and command issues. One of these can be expected to reverse over time. The other? Who knows. What I can tell you is that Gavin Floyd is not quite as good as his 2008 numbers might have you think, as the difference between his FIP and ERA is a staggering 1.32, and he has allowed 69 baserunners in his last 45 innings pitched.

Slight Advantage: Chicago

Starter, Game 4
BOS: Josh Beckett
CHI: John Danks

Danks is having a breakthrough season and is coming off of a nice start against the Tigers. Beckett is also on the wake of a decent start, and despite all of the talk-radio hand wringing he is carrying a FIP of 3.38. In his last start, 1/3 of his pitches were curveballs. If both of these guys are on, this will be an interesting matchup.

Slight Advantage: Boston

Infield
BOS: Kevin Youkilis, Dustin Pedroia, Mike Lowell, Jed Lowrie
CHI: Paul Konerko, Alexei Ramirez, Juan Uribe, Orlando Cabrera

It’s tough to properly gauge this matchup without knowing Youkilis’ status after injuring his hand last night. The official word is “day-to-day”, and Sean Casey would play if Kevin can’t. Either way, Boston has the advantage at 1B over the lifeless Konerko. It’s just a question of how wide the gap is. We’ll take the team’s explanation at face value and assume Youkilis plays.

Ramirez is the Rookie of the Year candidate you haven’t heard about. He’s old for a rookie, but the alleged 26-year-old is hitting .311/.330./478 while playing solid defense at second base. Pedroia continues to be one of the best players in baseball since mid-June, hitting .399/.439/.568 in his last 199 plate appearances. Juan Uribe is filling in for Joe Crede, who is at least a week from returning to the lineup. Mike Lowell looks like he should be sitting right now, as he is visibly hobbled and has hit .171/.222/.211 in his last 81 PAs.

In the event that Lowell can’t play, you’d see Jed Lowrie move over and Alex Cora playing SS. Jed Lowrie vs Orlando Cabrera is a very interesting comparison, as it pits offense against defense. Lowrie’s gap power has New Englanders hoping they never have to see Julio Lugo start another game in Red Sox uniform, while at the same time bemoaning Theo Epstein for not resigning the slick-fielding Cabrera after 2004.

Advantage: Boston

Outfield
BOS: Jason Bay, Jacoby Ellsbury, J.D. Drew, Coco Crisp, Brian Giles?
CHI: Carlos Quentin, Nick Swisher, Jermaine Dye, Ken Griffey Jr.
Jason Bay’s praises have been sung by many a minstrel, but Carlos Quentin is having just a phenomenal year in the American League, helping to dispel the notion that every National League player will automatically struggle after changing leagues. Both center fielders have been somewhat disappointing offensively this season. Ellsbury at least will cover a large amount of real estate in CF, but Swisher is clearly the more productive hitter (even when both players are playing to their potential). Jermaine Dye is a guy who has amazed me over the past few years. His shin bones are as frail as those from Barbaro’s rotting corpse, and yet the guy crushes the ball season after season. Despite the Red Sox outfield actually earning 1 more Win Share in total (46 vs 45), the run scoring potential of the White Sox outfield cannot be denied here.

Slight Advantage: Chicago

Catcher
BOS: Jason Varitek
CHI: A.J. Pierzynski

I’ll factor out pitch-calling abilities here, since those skills manifest themselves in the performance of the pitchers. Jason has shown a little more offensive prowess lately, hitting .262/.380/.405 in his last 50 plate appearances. Still he’s one of the last guys you’d want to see at the plate in a critical situation, whereas A.J. can handle the stick just fine.

Advantage: Chicago

Designated Hitter
BOS: David Ortiz
CHI: Jim Thome

Jim Thome at 37 years young is sporting a nifty slugging percentage of .517, which is actually his lowest in a full season in the past 15 years. Thome being on the decline is obvious and expected…but let’s now acknowledge the elephant in the corner. David Ortiz, who has the classic frame of the fearsome but short-lived extra large power hitter, is hitting .250/.327/.354 since returning from injury. His wrist issues are still affecting his swing, and he has seen his power numbers fall off the table in 2008. In their current states, Thome is the more productive hitter.

Slight Advantage: Chicago

Bullpen
BOS: Jonathan Papelbon, Hideki Okajima, Justin Masterson, David Aardsma, Javier Lopez, Mike Timlin
CHI: Bobby Jenks, Octavio Dotel, Matt Thornton, Boone Logan, Scott Linebrink

While Boston has a palpable advantage at the closer slot with Papelbon, Chicago’s set-up tandem of Dotel and Thornton is among the best in the game. Overall, the Red Sox bullpen has been relatively decent, with a 3.64 ERA and 7.73 K/9, but Chicago has the advantage with a 3.45 bullpen ERA and 8.3 K/9. To further the point, much of Boston’s bullpen value is tied up in Papelbon, whereas Chicago’s late-inning excellence is more evenly distributed between a group of four pitchers.

Slight Advantage: Chicago

OVERALL: A slight advantage goes to Boston, thanks mostly to a favorable matchup of starting pitchers and a clear advantage in the infield positions. A Chicago home-field advantage tilts the matchup to more even ground.

This should be a fun series, and it’s one that currently deserves more national press than a Red Sox / Yankees series would get right now.