Here is the position-by-position breakdown:

Catcher

Jorge Posada vs. Carlos Ruiz

Ironically, both catchers were signed as second basemen with bad feet, so they were moved behind the plate as pros.  Posada has seen and done it all, but he's had a tumultuous postseason.  His defense and pitcher management have been called into question and he's done little to prove his doubters wrong.  Meanwhile, he's hit like a 27-year-old catcher (he's 37) including two clutch homeruns.  Despite all his experience, he has to be the worst baserunner in this series.

Carlos Ruiz is the best damn career .246 hitter that I've ever seen.  For whatever reason, he is a brutal out in a clutch spot.  He outshines Posada in the leadership category and while I'd rather have Posada for a career or a season, I'd take Ruiz for the next seven games.

Advantage: Phillies

First Base

Mark Teixeira vs. Ryan Howard

Overall, Teixeira has struggled at the plate this October, although he's had his moments (ALDS Game 2 walk-off, ALCS Game 5 3-run double).  He's swinging the stick much better from the right-hand side, which is good news considering the Phils will feature lefty after lefty.  In the field, he's been the best defensive player of the postseason (any team, any position). 

Howard showed the ability to carry a team for an entire series.  Like A-Rod, Howard was immense in the LCS en route to an MVP trophy.  However, he hit just .207 against lefties this season and he'll see two good ones in CC Sabathia and Andy Pettitte.  The Yankees have fed off their opponents defensive miscues in the last two series and Howard is a liability at first base.

Advantage: Yankees

Second Base

Robinson Cano vs. Chase Utley

Cano is in good form coming into his first World Series.  He has hits in five straight games and has played a dynamic second base (ALCS Game 2 aside).  The national media would pick Utley in a walk over Cano, but the stats are much closer than you'd think.  Cano actually outslugged Utley .520 to .508 in the regular season.

Utley gets treated like the Derek Jeter of the Phillies thanks to his toughness.  He's coming off a rough NLCS in which he struggled defensively and drove in just one run.  On this stage though, I'd rather have Utley's experience than Cano's penchant for daydreaming.

Advantage: Phillies

Shortstop

Derek Jeter vs. Jimmy Rollins

Remember back to the World Baseball Classic, Jeter was getting treated like a charity case, while Rollins was considered the far better choice.  Not anymore.  Jeter is looking to put the finishing touches on one of his greatest seasons and win his 5th ring in the process.  Here's what people don't understand about Derek Jeter: He does not raise the level of his game in the postseason; he just plays HIS game despite the high pressure atmosphere.  He is a .317 career hitter and a .308 career postseason hitter.

Rollins has seen his game decline since his 2007 MVP season.  He had a below-average regular season for a player of his talent.  He came through with a big hit to win Game 4 of the NLCS off Jonathan Broxton, but he is homerless in the postseason.  Even worse, he has not stolen a base in the playoffs.  He'll have to terrorize the Yankees on the basepaths to be a factor in the World Series.

Advantage: Yankees

Third Base

Alex Rodriguez vs. Pedro Feliz

Alex Rodriguez has been the best player in baseball this month.  He is hitting every pitch square on the barrel.  Even better, he's not chasing bad pitches.  Unlike other sluggers, Rodriguez is a superior baserunner so walking him can be just as dangerous.  He'll likely come back to Earth in the Series, but his mere presence will give Teixeira, Posada and Hideki Matsui the chance to put up numbers. 

Feliz is the closest thing to a weak link the Phillies have.  He is a solid defensive player, but he does not bring a whole lot to the batter's box.  However, October is the time for unsung heroes.

Advantage: Yankees

Left Field

Johnny Damon vs. Raul Ibanez

Damon comes into his second World Series scorching hot at the plate.  He hit in all six ALCS games, including three multi-hit efforts.  Damon is a streak hitter in a great groove, but he can be handled by quality lefties.  He does not run much anymore as he has developed into a power hitter.  As an outfielder, he'd make for a great circus performer.

Ibanez is equally as brutal defensively, but also equally as dangerous at the plate.  He finished the NLCS cold (1/14) after a strong series against the Rockies (5 RBI).  He is a professional hitter that would do well in a DH role in New York.

Advantage: Push

Center Field

Melky Cabrera vs. Shane Victorino

Cabrera is an interesting player.  He is by far the least famous of the Yankees regular nine.  He is not a five-tool player, but he checks all the boxes.  He plays a solid center and has the strongest throwing arm among the outfielders.  He can run a little and occasionally smack a homer.  He tends to ride the confidence wave, but he should be sky high coming off a fantastic ALCS (9 hits). 

Victorino is a more polished version of Cabrera.  He does everything well, but nothing spectacularly well.  Outside of Howard, the Hawaiian has been the Phillies best player this postseason.  He had five multi-hit games and three homeruns in the two series combined.

Advantage: Phillies

Right Field

Nick Swisher vs. Jayson Werth

Swisher has been exposed in the playoffs.  He struggles with pitchers that feature good change-ups, which is pretty much the entire Philadelphia staff.  However, he has stayed focused, which is an issue at times, and played great defense so far. 

Werth has been the breakout star of the postseason.  He was a first round pick 12 years ago, but he's just now playing his best baseball.  Philly relies on worth to be a right-handed threat in a left-hand dominant lineup.  With five homeruns in his last eight games, he's done his job well.  He'll need to pop a Sabathia hanging slider at some point in the World Series for the Phils to steal one from the Yankees ace.

Advantage: Phillies

Designated Hitter/Pinch Hitters

Hideki Matsui vs. Matt Stairs

Matsui will be relegated to pinch hitting duty in the National League park, but he thrived in that role during interleague play.  These are likely his last games as a Yankee, so he'll want to go out on top.  As for the rest of the bench, Eric Hinske was added as another pinch hitter.  Brett Gardner struggled as a pinch runner in the ALCS, but he could terrorize Brad Lidge, who loathes holding runners on.  Jerry Hairston can play anywhere.  Just a guess, but I think Posada catches A.J. Burnett in Game 2, not Jose Molina.

Stairs is the Phillies primary pinch hitter, although Ben Francisco will likely get a Game 1 start in left or as the DH.  The Phillies don't have many threatening players in reserve with Eric Bruntlett and Paul Bako.

Advantage: Yankees