That stretch covers 65 games coming off the White Sox schedule and nine straight losses for the big right-hander as a member of the White Sox rotation.
But with one swing of the bat from Josh Fields in the seventh inning of Monday's rescheduled contest against Tampa Bay, Contreras saw his Major League-worst 17th loss this season almost instantly turn into his seventh victory.
Fields' two-run, two-out home run off reliever Dan Wheeler completed a four-home run, five-run White Sox rally in the seventh, giving the South Siders a 5-4 victory before a crowd approximately one-third the size of the announced 37,030 paid attendance at U.S. Cellular Field. Monday's effort also ended a five-game losing streak for the White Sox (57-74), who produced their 26th comeback win of the season and finished 6-1 in head-to-head matchups with the Devil Rays (51-80).
The White Sox clubhouse seemed loose and full of humor following Monday's win, ending this eight-game homestand with a 3-5 record. It was a far cry from the subdued atmosphere after Boston's weekend massacre.
"We are great in one-game series," said White Sox manager Ozzie Guillen, drawing a huge laugh from the media before his press conference. "This team won't give up or give in."
"It was nice to end the homestand on a win after the last weekend," added White Sox catcher A.J. Pierzynski, who knocked out two hits in the victory.
Despite Contreras (7-16) limiting the Devil Rays to four runs on eight hits over seven innings while matching a season-high with eight strikeouts, he finished the top of the seventh with 101 pitches and a 4-0 deficit staring back at him. Contreras' teammates quickly took him off the hook with a power explosion against Tampa Bay starter Edwin Jackson in the bottom of the frame, as Pierzynski (No. 13), Jermaine Dye (No. 26) and Juan Uribe (No. 15) went back-to-back-to-back in the span of nine pitches.
Prior to the seventh, the White Sox had managed five singles against the Tampa right-hander.
"We didn't look that great early on in the game, but A.J.'s home run sparked something in our team," said White Sox closer Bobby Jenks, who retired the side in order in the ninth for his 36th save, having now set down nine in a row and 50 of the last 51 opposing hitters he has faced.
"[Jackson] has pitched pretty well," Pierzynski added. "For that to happen is pretty surprising. It seemed like we were totally dead and out of nowhere, we came to life."
Danny Richar followed the trio of long balls with a double, and moved to third on a one-out wild pitch from Wheeler (0-2). The former Houston closer struck out Jerry Owens to protect the one-run lead, but Fields lined a 1-0 offering into the White Sox bullpen for his 17th home run in 74 games.
Fields launched a curve ball for the team's fourth home run in the seventh. The last time the White Sox cleared the fences four times in the same frame came on Aug. 21, 2005, when Tadahito Iguchi, Aaron Rowand, Paul Konerko and Chris Widger went deep against the Yankees and Randy Johnson.
At that point, they were facing a slightly higher caliber opposing pitcher and on their way to the franchise's first World Series title in almost nine decades. Monday's victory represented nothing more than pride.
"Every game is for pride from now on," said Fields, who did not have a defensive chance in left field during his second Major League start at the position. "It's more heart than anything. Guys want to end on the right note."
"I feel great I won a game," added Contreras through translator and bench coach Joey Cora. "I feel better I helped the team win a game."
When the White Sox and Devil Rays originally were scheduled to play this game on May 26, the South Siders were at a season-best 24-20 and sat four games back in third place in the American League Central. It has been a precipitous and painful slide to the bottom of the division from that rainout moving forward.
Contreras actually had a 4-4 record and 3.71 ERA back in late May, before slipping into a 1-12 abyss as a starter. For at least one more day, though, Contreras avoided another move closer to 20 losses or toward the franchise's most single-season losses since 1980 (LaMarr Hoyt's 18 in 1984).
His performance on Monday gave Contreras hope for a strong finish to 2007, the same hope the White Sox are clinging to as a team.
"Great game, and he's climbing every day," said Guillen of Contreras. "His fastball is coming around, and when he throws strikes with his fastball, his split-finger is good enough to put people away."
"I definitely saw he was better today," added Pierzynski of Contreras. "His ball had more life and it was coming out of his hand better. You could see the difference with strikeouts and swings and misses he was getting."
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.