For this exercise, I'm focusing on the Western Conference. I took a sample of six forwards from teams currently out of the playoffs, who are going to be unrestricted free agents after the season. I then went through their current statistics, and game-by-game logs, to determine their points-per-game production against each of the current Western Conference playoff teams, leaving the remainder in an "Other" category, representing what they've done against the dogs of the West, and the Eastern Conference overall. Within each player's row, I've shaded their most favorable matchup in green, and their least productive in pink. From the inquiring GM's perspective, they might focus on the columns, and see which players perform particularly well against likely playoff opponents.
I kept this within the West, due to the scarcity of interconference play; it's hard to say anything meaningful about a player/opponent pairing when they only play once a year.
Granted, teams won't be able to predict 1st-round matchups until we're closer to the playoffs, but one likely pairing will be Detroit and San Jose, presuming that Nashville and Anaheim win their respective divisions. If I'm Detroit GM Ken Holland, this table might suggest that Bill Guerin is more attractive than Keith Tkachuk, given their relative performance against the Sharks. If you're eyeing a series against the Ducks, the opposite holds true - power forwards like Tkachuk and Ryan Smyth have been more successful than the speedy Guerin. For a team looking to tangle with the Canucks, Smyth and Smolinski appear snakebit, and if preparing to face the Red Wings, none of these guys looks promising.
If I have a chance, I'll post a similar table for selected Eastern Conference players tomorrow. Until then, take a look and feel free to offer constructive criticisms in the comments!