And the postseason woes go back even further, all the way to 1990, when they lost the World Series to the Reds. They haven't been back, going 1-11 in potential clinch games -- Tuesday's 8-6 deficit in Detroit included.
Oakland also lost Game 5s in 2001, 2002, 2003 and 2012. Three times the A's held a two-game lead before dropping the next two. Perhaps there is solace in knowing Oakland dropped back-to-back games just once in its last 35 regular-season contests this year. But this is the postseason, a different kind of animal.
Still, the A's are keeping their heads high entering Thursday's elimination game, hoping for a better ending -- even after handing away Tuesday's game by way of one too many missed opportunities that could haunt the franchise much like past blunders have, notably the infamous "Slide, Jeremy, slide!" play of 2001.
The A's will turn to rookie Sonny Gray, just 23 years old, to try to turn the tables on Detroit's Justin Verlander, who won Game 5 in Oakland last year.
"I think we have confidence, especially knowing we're playing at home," Jed Lowrie said on Wednesday. "We know what we're up against in Justin Verlander, but I think we're all prepared and know that it's a winner-take-all scenario and everybody will be ready to go."
"We have gone through a lot of difficult losses over the last two years and we've been able to respond," said manager Bob Melvin. "That shows me it's a resilient group that's intent on winning on any particular day."
The A's didn't score off Verlander in Game 2 on Saturday over seven innings, and they failed to get a run off him in last year's Game 5, when he notched a complete-game victory with 11 strikeouts. But they have beaten him, and not too long ago, tagging him for five runs (three earned) on four hits in five innings in Detroit on Aug. 27.
Oakland forced Verlander to throw 44 pitches in a two-run first and 104 in all. Getting to him early is paramount.
"I think the strength of our offense all year has been to trust everybody up and down the lineup and not try to do too much," Lowrie said "That's the easiest way to get to a guy like Verlander, give yourself as many opportunities to score as possible. Get guys on base and get him to throw those stress innings and pitches where he's not able to cruise through innings."
"He's been beat before I think, so we're going to try to go out and do it again," Josh Donaldson said. "He's a good pitcher. We have a good lineup. And we get to play at home."
Last season, the Division Series was oddly structured, with the higher-seeded team opening on the road, as the A's did in Detroit and dropped the first two games. Only then did they return to Oakland to force and, ultimately, lose Game 5.
So not even home-field advantage has been able to save the A's in the past. In fact, they had it in their last four postseason defeats: the 2002 ALDS vs. Twins, the 2003 ALDS vs. the Red Sox, and the 2006 ALCS and 2012 ALDS vs. the Tigers.
"But this is a different team," noted lefty Brett Anderson. "It's the same situation but a different team. I like the way we've been playing and feel confident we can get the job done at the end. We get a chance to be home and celebrate at home."