The knuckleballer last pitched on Aug. 6 in Kansas City before being placed on the disabled list with tightness in the back of his right shoulder.
Though manager Terry Francona has yet to make a final determination, Wakefield could return next week in New York, when the Red Sox play a three-game series against the Yankees, Aug. 26-28.
Part of it could depend on whether Josh Beckett, who has been dealing with some numbness in two of his right fingers, makes his scheduled start against the Yankees on Tuesday.
"I wouldn't rule [Wakefield] out," Francona said. "We need to see a lot of things. One of those is how he's doing also. He threw 44 pitches today on the side and did well. He will throw another side on Saturday. Then that kind of hopefully puts him in line to us thinking about starting him in a game. That's kind of where we're at. With the days off, [with] Beckett, we have some ability to maneuver this and manipulate it a little bit. We'll just kind of take stock on where everybody is and plug them in."
Just as the Red Sox had hoped, the down time has served Wakefield well.
"[I'm] pain free," said Wakefield. "Everything felt good. I'm going to throw another side on Saturday and see how it feels and go from there."
Wakefield has been one of Boston's most consistent starters all year long, going 7-8 with a 3.67 ERA. He is tied with Jon Lester for the team lead in quality starts with 16.
This is the second year in a row Wakefield has suffered a late-season arm injury. But he noted that the team took a more conservative approach this time around. A year ago, Wakefield missed just one start during the regular season, but wound up being inactive for both the American League Division Series and the World Series.
"Last year was a situation where we were in the middle of a pennant race -- not that we're not in the middle of one now -- but we didn't have a whole lot of options," Wakefield said. "I had to pitch, and I tried to grit my teeth until I couldn't go anymore. It got so bad, the rest that was needed was longer than expected."
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.