With the first regular-season game just three days away, it is clear Tim Wakefield, who has been with the Red Sox longer than any current player, will not be receiving a contract extension that will take him past this season, leaving his future with the team in question.

While the Sox made little effort to re-sign their other potential free agents this spring -- most notably, center fielder Johnny Damon, who has said he will be looking for at least a four-year deal and would prefer six years in a new contract -- discussions about a contract extension for Wakefield quietly took place this spring between general manager Theo Epstein and the pitcher's agent, Barry Meister.

Wakefield is in the final year of a three-year, $13.02 million deal that calls for him to be paid $4.67 million this season. The knuckleballer, who turns 39 in August, would not talk about his discussions with the club, but in the past, while indicating a preference to end his career in Boston, he has made it clear he would not look for a major bump in salary.

The Sox, who told all of their pending free agents they would be asked to take a considerable discount to sign now as opposed to the end of the season, only offered Wakefield a one-year deal, according to industry sources, that involved a mutual option. Wakefield would have been paid at one price if the Sox exercised their option, and at a lesser figure if they declined the club option and Wakefield accepted a player option. If both parties declined, Wakefield would have been a free agent. That was not acceptable to Wakefield, the industry sources said, and the expectation is that the sides will talk after the season.

The Sox already have five starting pitchers under their contractual control in 2006 -- Curt Schilling, Matt Clement, and David Wells all have multiyear deals, and Wade Miller and Bronson Arroyo have fewer than the six years' experience required for free agency.

Thus, Wakefield, who was 12-10 with a 4.87 ERA last season in 30 starts and ranks eighth in wins on the Sox' all-time list with 114, could be odd man out, though Sox owners have said they hope to keep Wakefield, one of the most civic-minded Sox players, in a Boston uniform for the remainder of his career.

"I don't have any comment on negotiations," Meister said yesterday. "I don't do my business in public." Other Sox players who could be free agents after the season include third baseman Bill Mueller, first baseman Kevin Millar, and relievers Alan Embree and Mike Timlin.