After it seemed like a near certainty weeks ago, Wakefield will take his record eighth stab at No. 200 on Tuesday at Fenway Park when the division-rival Blue Jays come to town to kick off a brief two-game set.
The Red Sox, who have lost four straight series for the first time this year, could use any kind of positive momentum swing they can muster.
Beginning a critical 10-game homestand -- their last of the regular season -- the Sox's American League Wild Card lead over the Rays continues to dwindle after Tampa Bay swept the weekend series and won on Monday in Baltimore, narrowing Boston's lead over Tampa Bay in the standings to three games.
Boston has dropped five straight, its longest losing streak since starting 0-6 to open the season.
Toronto, which has won five of seven and has emerged victorious in back-to-back series for the first time since Aug. 12-17, will look to play spoiler as Boston aims to clinch it seventh playoff berth since 2003.
Wakefield left his last outing with a three-run lead before reliever Daniel Bard had a rare meltdown and the Red Sox fell, 11-10, to the Blue Jays.
"I struggled the first three innings throwing strikes and put a lot of pressure on those guys from the sixth on to the ninth," Wakefield said afterward. "I'll take the blame for not getting deeper into the game to give those guys a little bit of rest."
In his seven-game quest to become the 89th pitcher in baseball's modern era (since 1900) to win 200 games, Wakefield has left with the lead three times only to have the bullpen squander it.
"If it happens, it happens," Wakefield said. "If it doesn't, it doesn't change what I've done. I'd like it to happen, but more importantly is for us to get in the postseason."
To do so, it'd help if the Red Sox could get back on track Tuesday against Brandon Morrow and the Blue Jays.
Morrow, who allowed eight runs in 4 1/3 innings during his last start against Boston, has surrendered 22 earned runs in his last 20 1/3 innings of work and is winless since Aug. 17.
"It has been a really frustrating stretch of starts," said Morrow, who has surrendered eight home runs in his past four starts. "It's just something that I'm trying to learn from. The problem has been getting the fastball to the first-base side of the plate."
Blue Jays: A solid impact
In his first 36 games with Toronto, Brett Lawrie has made quite the splash.
Since his debut on Aug. 5, he has racked up four triples, nine homers, 21 extra-base hits and 82 total bases.
The only other active players to hit nine homers and drive in 22 runs in their first 35 games of Major League service are Albert Pujols (12 homers, 39 RBIs), Adam Dunn (11, 31), Chris Davis (11, 26) and Jeff Francoeur (10, 30).
Jose Bautista has reached base safely in 122 of his 134 games this year.
Red Sox: Tops at the top
Red Sox leadoff man Jacoby Ellsbury has been a remarkable spark at the top of Boston's lineup, having hit safely in his last 16 games.
Ellsbury, who turned 28 on Sunday and is an emerging candidate for the AL MVP Award, is hitting .353 (24-for-68) in that span with 10 doubles, a triple, three homers, 10 RBIs and 11 runs.
Ellsbury is a .333 (115-for-345) hitter in September, the best batting average of any month of his career.
Kevin Youkilis will join the team when it returns to Boston. He was diagnosed with bursitis in his left hip, and he was given a cortisone shot on Friday.
Starting with the recently-completed road trip, the Red Sox's final 23 games all come against AL East rivals. Entering Sunday, Boston had the best record against the division among all AL teams.
The Blue Jays' record has stood at .500 on 30 different occasions this season, the most in the Major Leagues.