Losing 12 of the first 19 games during that stretch, in fact, left their well of potential prosperity looking pretty dry.
So anything, even a small trickle on Wednesday night, would go a long way toward restoring some semblance of hope as Chicago closed out its 20-day odyssey and closed in on the final three weeks of the regular season.
Consider Wednesday's result, then, a surge in the right direction.
A.J. Pierzynski hit a walk-off double off the center-field wall in the 13th inning to send the White Sox past the A's, 4-3, on Wednesday night at U.S. Cellular Field and salvage a split of the two-game set. Pierzynski's hit scored Alexei Ramirez, who delivered a one-out single to center, from first base.
Coupled with Detroit's 5-1 loss to Kansas City, the White Sox moved to within 6 1/2 games of the first-place Tigers. Chicago picked up its first full game on Detroit since Aug. 22.
It only seems like an eternity since something went Chicago's way in its quest to reach first place in the American League Central.
"We have to just try to keep winning games and forget a little bit about Detroit," White Sox reliever Octavio Dotel said. "Hopefully they lose, but we can't worry about them. Just think about ourselves and try to do our best -- that's all we can control."
Dotel (3-3) was the pitching hero on Wednesday night, tossing the final three innings of the contest to pick up the victory. He threw three frames for the first time since Aug. 6, 2004, against Minnesota.
"I tip my hat to him because it's the first time he's thrown three innings in a long time -- maybe in 10 years," White Sox manger Ozzie Guillen said. "And he gives me those innings. He was pretty good. Dotel did a tremendous job today."
Of course, the White Sox wouldn't have needed Dotel's services if not for blowing a 3-2 lead in the eighth inning.
Guillen pulled left-handed reliever Matt Thornton with two outs in the eighth inning -- trying to preserve Thornton's overworked arm -- despite the fact he had retired all five batters he faced. Guillen put in right-hander Tony Pena, who immediately ran into trouble. Pena surrendered a double to Scott Hairston and a single back up the box from Kurt Suzuki, which tied the game at 3.
Guillen defended the move following the contest.
"You look at the way Matt Thornton is pitching for us, I'm not going to ruin this guy's career pitching him 30 pitches every time he goes out there," Guillen said. "I've got to rely on the bullpen, and [not] just ... one guy in the bullpen. I bring the righty in just to face two guys. He couldn't get anybody out. After that, it's history."
With the game still tied after 10 innings, Guillen opted for Dotel, who rewarded his manager for that decision.
"I asked [pitching coach Don] Cooper and Ozzie to leave me out there and see what happens," Dotel said. "The bullpen threw a lot, so I'm trying to give some rest to some guys over there. But the main thing was where we are at and what we are trying to do and where we are trying to get. That's the reason I asked Cooper and Ozzie to give me one more."
Before any of the team's relievers made an appearance, White Sox pitcher Freddy Garcia made his case for becoming the prime candidate for Chicago's fifth starter role next season. He lasted six innings, scattering two runs on five hits with five strikeouts, which tied his season high. He now has produced four straight quality starts.
"The way he throws, it always gives us a chance to win the game," Guillen said.
The White Sox squandered one of their better late-inning opportunities to score in the 11th inning. Chicago loaded the bases with two outs for Jermaine Dye, but Dye grounded into a fielder's choice to Oakland second baseman Mark Ellis.
Two innings later, Pierzynski made that out a moot point by driving the game-winning hit over A's center fielder Rajai Davis.
Even though the White Sox finished their 20 games in 20 days stretch at 8-12, they ended their homestand at 4-2.
Could Pierzynski's late-inning heroics be enough to boost the White Sox into playoff contention?
"We hope so," Pierzynski said. "But we just don't know. We need help. We need Detroit to lose some games. We need Minnesota to lose some games. And we've got to go play well. If we do, anything can happen. We just need to win as many games as we can these last few and see what happens."
Jesse Temple is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.