For the first time since 2008, Chicago has neither a hockey team nor a basketball team in the second round of the playoffs. The Bulls are licking their wounds, the Blackhawks are bickering, and Patrick Kane is auditioning for the role of Lindsay Lohan.

But, as the saying goes, it could always be worse. How much worse? Here is our lineup of the ten most depressing playoff losses in Chicago sports history.

Honorable Mention: Blackhawks, 1991

The Hawks—led by Ed Belfour, Steve Larmer, Chris Chelios and Jeremy Roenick—were hockey’s best regular season team, winning the President’s Trophy. But instead of delivering a lengthy playoff run, Minnesota and its 27 regular season wins sent Chicago packing after six games. The Hawks took a 2-1 series lead, but the Stars won three in a row on their way to the Cup finals. “It’s like a bad dream when you’re hoping to wake up,” defenseman Steve Konroyd said after the Game 6 loss.

10) Cubs, 2008

The Cubs breaking their World Series drought in its 100th season turned out to be too poetic. But until October it seemed, if not likely, at least possible. The Cubs won 97 games with a veteran lineup and solid starting pitching under the steady hand of Lou Piniella. Then the Dodgers showed up at Wrigley Field and it all fell apart. Ryan Dempster walked seven in Game 1 and the Cubs made four errors in Game 2. L.A. won the next game 3-1 to complete the sweep. The Tribune’s headline the next day was almost as bad as the news it delivered: “You’ve all heard this punch line: But joke’s on Cubs for umpteenth time.” At least the Cubs didn’t do anything embarrassing—like sprinkle holy water on the dugout ahead of the series.

9) Bulls, 1975

Nine years before No. 23 suited up at the Madhouse on Madison, the Bulls were a game away from the NBA Finals. The only division winning team for the nucleus of Jerry Sloan, Norm Van Lier, and Bob Love, the Bulls led the NBA in defense during the regular season. They held a 3-2 series lead against Rick Barry and Golden State in the western conference finals in what Tribune sportswriter Bill Jauss called a “pulsating, punishing” series. A record crowd of 19,564 watched the Bulls lose Game 6 at Chicago Stadium 86-72. For an encore, the Bulls would blow an 11-point halftime lead in Game 7 on the road.

8) DePaul, 1980, 1981, 1982

The Ray Meyer led Blue Demons made the Final Four in 1979, earned a No. 1 seed in the next three NCAA tournaments and didn’t win a game in any of them. After first-round byes, they were upset in successive seasons by UCLA, St. Joseph’s, and Boston College. While it’s hard to imagine DePaul capturing the city’s imagination today, the early ‘80s were lean years for our professional franchises and DePaul was a national powerhouse with stars like Mark Aguirre and Terry Cummings. After completing the hat trick, Meyer said, “Normal for us. We go back with our tails between our legs and our heads down. Normal postseason basketball game for us.”

7) Bears, 1986, 1987

The two teams that followed the Super Bowl Shuffling Bears shared similar fates: lofty expectations, division championships, and home playoff losses to the Washington Redskins. The ’86 team went 14-2, but with Jim McMahon injured Mike Ditka called on Boston College sweetheart Doug Flutie at quarterback in the divisional round. Flutie went 11-for-31 with two picks as Washington won 27-13.

The next year, the Bears again hosted the Redskins at Soldier Field. With Joe Montana and the 49ers already out of the playoffs, the Bears had a clear path to the Super Bowl. But with the temperature at -3 degrees, the Bears squandered a14-0 lead and Washington won 21-17. The indelible image from the game: Walter Payton, in his last game as a Bear, catching a McMahon pass on fourth-and-eight, but coming up a yard short of the first down to seal the loss.

6) White Sox, 1983

The “Winnin’ Ugly” Sox started off 16-24 and then went an incredible 83-39 to win the AL West by 20 games. The Sox scored a league best 800 runs in the regular season behind Messrs. Fisk, Luzinski, Baines and Rookie of the Year Ron Kittle. Then came the playoffs against the Orioles and they scored three runs in four games. Kittle missed Game 4 after he was hit on the knee by a Mike Flanagan 3-0 pitch in Game 3. Kittle still claims Flanagan did it on purpose. In Game 4, Jerry Dybzinski overran second base, nullifying a seventh-inning rally and the Sox lost the clincher 3-0 in 10 innings at Old Comiskey.

5) Bulls, 2012

We’ll never know if the Bulls had the firepower to overcome Miami, but it sure would have been fun to find out. Instead, we’re stuck replaying the nightmare of our hometown star, Derrick Rose, writhing in pain under the basket after tearing his ACL. Adding injury to injury, Joakim Noah sprained his ankle in Game 3 and the Bulls lost to the Philadelphia 76ers 4-2, becoming just the fifth No. 1 seed to lose to an eighth-seed. Perhaps the cruelest irony of all was listening to Coach Tom Thibodeau repeat the mantra, “We have more than enough to win with.” It was true until it wasn’t.

4) Cubs, 1984

In a year the White Sox were supposed to be Chicago’s World Series contenders, the Cubs came out of nowhere to win the NL East, earning their first playoff appearance in 39 years. In the opening two games at Wrigley, they played like they belonged, too, winning 13-0 and 4-2 against the San Diego Padres. The Padres won the next two in California, but the Cubs took a 3-0 lead in Game 5 with eventual Cy Young winner Rick Sutcliffe on the mound. It wouldn’t last. The Padres scored two in the sixth inning and four in the seventh, aided by a ground ball that went through the legs of first baseman Leon Durham. In true Cubs fashion, 150 fans still showed up at O’Hare to welcome the losing team back to Chicago. “We came to greet them and say not to worry,” one fan said. “We still love them because we know they’ll be back next year.”

3) Blackhawks, 1971

The Hawks took a 2-0 lead against the mighty Canadiens, but Montreal fought back to force Game 7 at Chicago Stadium. The Hawks grabbed a 2-0 lead and came inches away from making it 3-0 when a Bobby Hull shot hit the crossbar in the second period. The game turned on a Jacques Lemaire slapshot from center ice that beat Hawks goalie Tony Esposito. Montreal would score twice more for a 3-2 win. “What is there to say?” Hull said after the game. “We had the lead in the series by a game, and the lead in this game by two goals, and we lose.” That sums it up.

2) Cubs, 2003

The Cubs, not pre-season favorites, rode the arms of Mark Prior and Kerry Wood to contention. The additions of Kenny Lofton and Aramis Ramirez at the trade deadline turned the Cubs into World Series hopefuls. The Cubs beat Atlanta in the Division Series and took a 3-1 series lead on the Florida Marlins in the NLCS. After a Game 5 loss in Miami, they returned to Chicago with Prior and Wood on the mound for Games 6 and 7. The eighth inning of Game 6 is now the stuff of Greek tragedy: Oh, Bartman! Oh, Gonzalez! The very next night, a Moises Alou home run gave the Cubs a 5-3 third inning lead. But of course there would be no happy ending. Marlins 9, Cubs 6.

1) White Sox, 1919

The World Series loss to the Cincinnati Reds wasn’t nearly as painful as the fallout: a thrown World Series that still taints the franchise. It also robbed Chicago of watching Joe Jackson hit, surely one of the greatest pleasures this town has ever known. The Reds won Game 8 in Chicago on the 38th anniversary of the Great Chicago Fire. Afterward, the Tribune proclaimed it had been “the world’s greatest world’s series.” Little did they know.

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DANIEL I. DORFMAN is a freelance sportswriter living in Chicago.