#14—WOUNDED WARRIOR: An ailing Michael Jordan stumbles into the arms of teammate Scottie Pippen after the Bulls' Game 5 of the NBA finals against the Utah Jazz. For more photos of great Chicago sports moments, check out the photo gallery »

Chicago is a Bears town. It’s also a Sox, Cubs, Hawks, and Bulls town. (We also like a good horserace, a fierce prizefight, and the occasional Olympic moment.) In good and (more often) bad times, we remain rabid about our sports teams: second-guessing our coaches, criticizing our players, and all too rarely reveling in a championship season.

So now that we have assembled our roster of the 40 most memorable and significant Chicago sports moments, is there any reason to expect it will be greeted with equanimity? Hell, no! Let the disputes begin—preferably over a cold beer at a local tavern. Once you’ve figured out where we went terribly wrong, let us know in the comments section below.

PLUS: Check out some great Chicago sports moments in our photo gallery »

40. Plaintive Plea
September 28, 1920
One of Chicago’s most memorable sports moments might be apocryphal: After White Sox left fielder “Shoeless” Joe Jackson concluded his testimony before a grand jury about throwing the World Series, a young boy confronted him and pleaded, “Say it ain’t so, Joe”—a remark that would come to symbolize the ugly Black Sox scandal of 1919.

39. Flivver Follies
November 28, 1895
Beginning at about 9 a.m. on Thanksgiving Day, with six inches of snow on the rutted streets, six cars took off from Chicago’s Jackson Park in the country’s first organized automobile race. Ten hours and 17 minutes later, after completing the 55-mile roundtrip to Evanston, the car built and driven by Frank Duryea was pushed across the finish line to take the $2,000 first prize.

38. Municipal Pastime
November 30, 1887
When football fans inside the gym at Chicago’s Farragut Boat Club learned that Yale’s Bulldogs had defeated the Harvard Crimson, an exultant Yale man tossed a boxing glove at a Harvard alum, who swung at it with a broomstick. With the glove bound up like a ball, a full-fledged game ensued—final score: 43–42, though nobody remembers who won—and softball was born.

37. NIT Picker
March 26, 1945
When the National Invitational Tournament still decided college basketball’s champion, DePaul University’s George Mikan, the team’s six-foot-ten center, set several scoring records— including 53 points in a semifinal victory over Rhode Island State—en route to DePaul’s stomping Bowling Green of Ohio 71–54 in the final at Madison Square Garden. For more on Mikan, watch the video below:

36. Crash of ’29
October 12, 1929
A few weeks before the stock market crash ushered in the Great Depression, the Cubs suffered “the greatest debacle, the most terrific flop” in World Series history, according to a Tribune account. Leading the Philadelphia A’s 8–0 in Game 4 of the series, the Cubs surrendered ten runs in a nightmare seventh inning and lost the game. Fueling the meltdown was center fielder Hack Wilson, who lost two routine fly balls in the sun in the inning—the second rolling to the wall for a three-run homer—putting him “at the head of the list of world series goats,” the Trib said. He would not be the last goat to spoil a Cubs postseason. For footage of the series, watch the video below:

35. Purple Power
September 2, 1995
On fourth and two at the Notre Dame 44, Fighting Irish running back Robert Farmer plowed into a purple wall of Northwestern defenders for a gain of only one yard. A capacity crowd at Notre Dame Stadium then watched in shock as Northwestern ran out the clock for a 17–15 victory. The perennial patsies of college football (23 straight losing seasons), the Wildcats had just pulled off “The Upset of the Century,” as the Sun-Times proclaimed, against the ninth-ranked, 27-point favorite, football powerhouse Notre Dame. But in the weeks ahead, Northwestern proved this was no fluke, going undefeated in the Big Ten and earning the school’s first Rose Bowl berth (a tense 41–32 loss to USC) since 1949. Watch NU's victory unfold in the video below:

34. Tarzan in Paris
July 20, 1924
The 20-year-old star of the Illinois Athletic Club, Johnny Weissmuller had been shattering swimming records—including those held by Hawaii’s Duke Kahanamoku—since he began competing in 1921. For the first of his three gold medals at the summer Olympics in Paris in 1924, the future movie Tarzan set a new Olympic record in the 100-meter freestyle with a time of 59 seconds. His teammate Kahanamoku trailed him by more than two seconds to take the silver.

33. Ice Breaker
March 12, 1966
When the Blackhawks met the New York Rangers at the Chicago Stadium, only three NHL players had ever scored 50 goals in a season: Rocket Richard, Boom Boom Geoffrion, and the Hawks’ Bobby Hull. For years that 50-goal plateau had seemed insurmountable—yet five and a half minutes into the third period, the Golden Jet, poised at center ice, sent a slap shot past Ranger goalie Cesare Maniago, giving Hull his magical 51st goal (he’d end up with 54 for the season). The Hawks went on to win 4–2, but only after a long delay to clear the ice of all the debris tossed by ecstatic hometown fans. Watch Hull's goal below:

32. Cat o’ ’69 Tales
September 9, 1969
The comfortable lead that the first-place Cubs had enjoyed throughout the summer of 1969 was almost gone when they played the surging Mets in a crucial late-season game in New York. In the first inning, a black cat darted past Ron Santo, the Cubs’ on-deck hitter, and through the Cubs’ dugout. The Cubs lost the game, fell out of first place the next day, and collapsed down the stretch. The ill fortune portended by the cat was “just stupid superstition, right?” asked the Tribune. Right.

31. Cardinal Virtue
December 28, 1947
Two weeks after defeating the Bears for the NFL’s western division championship, the Cardinals—Chicago’s other football team—faced the Philadelphia Eagles at frigid Comiskey Park for the title. After three exciting TD runs by the team’s “Dream Backfield”—including a 75-yard punt return by the future Hall of Famer Charley Trippi—the Cards clinched what would be a 28–21 victory with a 70-yard run up the middle by Elmer Angsman—giving him an average of 15.9 yards per carry, still a single-game playoff record. For more on Trippi, watch the video below:

Photograph: Chicago Tribune photo by Nuccio Di Nuzzo

30. Getting a Grip
December 9, 1934
On the frozen turf at New York’s Polo Grounds, the powerhouse Bears led the Giants 10–3 and seemed poised to win their third straight NFL championship. But at halftime, the Giants changed into sneakers their equipment manager had scrounged from Manhattan College’s basketball team. Surer of foot in the second half, the Giants ran away with what came to be known as the Sneakers Game, beating the slip-sliding Bears 30–13. For more on the Sneakers Game, watch the video below:

29. Loving Cup
April 10, 1961
Making their first appearance in the Stanley Cup finals since 1944, the youthful Chicago Blackhawks defeated Gordie Howe’s Detroit Red Wings, taking the series in six games. A quintessential moment came at the Chicago Stadium in the second period of the third game, when the Hawks scored three goals in six minutes and 23 seconds—a barrage ignited by 20-year-old Stan Mikita off a pass from his 22-year-old teammate, Bobby Hull. With Glenn Hall—Mr. Goalie—minding the net, the Hawks had all the makings of a dynasty, but despite three more trips together to the finals by Mikita and Hull, the two superstars would never again hoist Lord Stanley’s cup.

28. Wowee Wedgie
August 9, 1953
Viewers of the first nationally televised golf tournament were treated to one of the sport’s most dramatic finishes when Lew Worsham—trailing Chandler Harper by one shot in the World Championship of Golf at the Tam O’Shanter Country Club in Niles—used a wedge to drive his ball 130 feet from the fairway to the cup for an eagle (and the tourney’s $25,000 first prize) on the course’s four-par, 410-yard 18th hole.

27. One-Man Team
November 23, 1935
Down 6–0 late in the third quarter at the University of Illinois’s Memorial Stadium, the University of Chicago Maroons turned to their captain, Jay Berwanger, who was playing his last game with the team. Wasting no time, Berwanger shook off five tacklers to return a punt 49 yards to the Illini one-yard line. Three plays later, he leaped over the Illini defenders, tumbled into the end zone for the touchdown—and then kicked the extra point to give the Maroons a 7–6 lead. That score would hold, and at the game’s conclusion, Berwanger’s teammates carried him off the field in triumph. Seventeen days later in New York, Berwanger became the first recipient of the Heisman Trophy (known then as the Downtown Athletic Club Trophy).

26. Special K
May 6, 1998
As rain fell in the ninth inning at Wrigley Field, Kerry Wood, the Cubs’ 20-year-old pitching phenom, threw a parabolic curve ball to the Houston Astros’ Derek Bell, who swung and missed. In only his fifth major-league start, Wood had just struck out his 20th batter of the day, tying the major-league record for a nine-inning game. Wood walked none and gave up just one hit, a weak infield grounder that could have been ruled an error. It was the most dominant and electrifying pitching performance ever at Wrigley Field. Watch Wood discuss his 20K game below:

25. Sweetness Indeed
November 20, 1977
Twenty years before Michael Jordan’s legendary “flu game,” Walter Payton approached the kickoff against the Minnesota Vikings feeling queasy after suffering from the flu for several days. Yet he pounded the Vikings for 275 yards, setting an NFL single-game record that would stand for 23 years. Sick as he was, Payton saved his best for the fourth quarter—a 58-yard burst that helped seal this performance as one for the ages.

24. City Series
October 9, 1906
In 1906, the Cubs won 116 games during the regular season—a record that still stands—and went on to face the White Sox, dubbed the “hitless wonders” by the Tribune’s Hugh Fullerton, in the World Series. But in the fifth inning of the first game—held amid snow flurries at the Cubs’ West Side Park (near Polk and Wood streets)—Cubs catcher Johnny Kling dropped a throw to the plate, allowing Sox third baseman George Rohe, a last-minute replacement, to score the game’s first run. The Sox went on to win the pitching duel 2–1 and ultimately triumphed over the highly favored Cubs in six games—just as Fullerton had predicted. For more on the Cubs' Kling, watch the video below:

23. Bearing Down
December 29, 1963
Clinging to a 14–10 lead with just ten seconds to play in the 1963 championship game, the Bears were fighting to stop the New York Giants from scoring the go-ahead touchdown. That’s when the Bears’ Richie Petitbon intercepted a pass from Giants quarterback Y. A. Tittle—the defense’s fifth pick of the afternoon—assuring an end to the team’s 17-year championship drought. The Bears wouldn’t win another NFL title until the 1986 Super Bowl.

22. Net Work
March 22, 1958
Inside Huff Gym in downstate Champaign during the finals of the 1958 Illinois high-school basketball tournament, the Marshall Commandos, having fought back from a fourth-quarter deficit, took a 60–59 lead over the favored Rock Falls Rockets when Bobby Jones sank a one-handed jumper from 20 feet out. The undefeated Commandos, an all-black squad coached by Isadore “Spin” Solario, went on to win 70–64, giving Chicago its first state championship.

21. Horse Play
August 31, 1955
At Homewood’s Washington Park Race Track, the thoroughbred Nashua, winner of the 1955 Preakness and the Belmont Stakes, went head to head in a match race against the chestnut colt Swaps, winner of the Kentucky Derby. Wielding his whip, the jockey Eddie Arcaro drove Nashua quickly out of the gate, a strategic move that gave the big bay an early lead. Riding Swaps (who was nursing an injured hoof), Willie Shoemaker couldn’t make up the lost ground, and Nashua won the mile-and-a-quarter race—and the $100,000 pot—by six and a half lengths. Watch the video below:

20. Gored Bull
October 7, 1984
Cubs first baseman Leon “Bull” Durham committed only four errors during the 1984 season, none on ground balls. But with the Cubs clinging to a 3–2 lead in the seventh inning of the deciding game of the National League playoffs against the San Diego Padres, Durham watched a ground ball roll between his legs, allowing the tying run to score and putting the go-ahead run on first base. Other Cubs contributed to the Padres’ four-run eruption that inning, but Durham’s miscue was pivotal, and stunned Cubs fans were forced yet again to wait till next year. Watch Durham's error at MLB.com »

19. Unlikely Hero
June 20, 1993
It wasn’t Jordan. It wasn’t even Scottie Pippen. No, the Bulls won their third straight NBA championship when John Paxson calmly buried a three-point shot with 3.9 seconds to go in Game 6 against the Phoenix Suns. It was the quintessential game winner, and the moment kids imagine when they practice in the driveway. “It’s a dream,” Paxson told reporters. Watch his shot in the video below:

18. Five Outs to Go!
October 14, 2003
Leading the Florida Marlins 3–0 in the eighth inning of Game 6 of the National League Championship Series, the Cubs seemed certain to reach the World Series for the first time in more than half a century. But with one out, a fan named Steve Bartman reached up and deflected a foul pop, possibly preventing left fielder Moises Alou from catching the ball for the second out. From there things turned surreal: a walk, an error on a double-play ball, a barrage of hits, and eight Marlins runs crossing the plate. As they had done for generations, the Cubs watched the World Series on TV that year.

17. Called Shot
October 1, 1932
Cubs players were “razzing” Babe Ruth with “very peppery” taunts, the Tribune reported, when the Yankees slugger batted in the fifth inning of Game 3 of the 1932 World Series. With two strikes, Ruth raised his right arm and pointed, then blasted Charley Root’s next pitch to center field for a home run. Later, some observers (and Ruth) claimed the Babe had called his shot by pointing to center field and hitting it there. Others, including Root, argued otherwise. The debate over one of baseball’s most famous moments May never be resolved. For more on Ruth's called shot, watch MLB.com's video »

16. Off Center
January 1, 1949
In the waning minutes of the Rose Bowl, Northwestern University’s Wildcats lined up at Cal’s 43-yard line and resorted to a trick play: Alex Sarkisian, the Wildcat center, snapped the football directly to halfback Ed Tunnicliff, who took it in for a touchdown and a 20–14 triumph. Watch footage of the play below:

15. Vikings Punk’d
September 19, 1985
In the third quarter of the third game of the 1985 season, with the Bears losing 17–9 to the Minnesota Vikings, coach Mike Ditka gambled, yanking backup quarterback Steve Fuller and inserting starter Jim McMahon, sidelined until then with a bad back. On his first play, McMahon hit Willie Gault for a 70-yard touchdown. On the next possession, McMahon threw another touchdown, and the Bears went on to win 33–24. The 1985 campaign would be filled with highlights, but that early-season comeback was the “quantum leap,” as safety Gary Fencik later explained, toward an eventual Super Bowl victory. Watch McMahon lead the Bears' comeback below:

14. Wounded Warrior
June 11, 1997
Before Game 5 of the NBA finals against the Utah Jazz, Michael Jordan was so ill his teammates wondered if he could play. Appearing wan and woozy, Jordan played. At times he seemed on the verge of collapse, only to gather his strength and attack the basket or flick in a fade-away jumper. He finished with 38 points, including the game winner. The pivotal victory put the Bulls up three games to two en route to their fifth championship. When the game ended, Jordan stumbled into the arms of his teammate Scottie Pippen, who held him upright even as MJ’s legend soared to a new level. Watch Jordan play through his flu below:

13. Evers’s Brainstorm
September 23, 1908
Late in the 1908 season, the Cubs appeared to lose a critical game against the New York Giants. But Cubs second baseman Johnny Evers noticed that the runner on first, Fred Merkle, had failed to advance to second base on the game-winning hit before heading to the clubhouse. Evers got the ball and stepped on second. The ump called Merkle out on a force play, and because the game ended in a tie, it had to be replayed (the Cubs won the rematch). The play went down in baseball infamy as Merkle’s Boner, but only Evers’s alertness made it possible. His quick thinking ultimately enabled the Cubs to reach the 1908 World Series—the last they have won. For more on Merkle, watch the video below:

12. Leap of Faith
July 23, 2009
With nobody out in the top of the ninth inning at U.S. Cellular Field, White Sox center fielder Dewayne Wise, inserted as a defensive replacement, made a spectacular leaping catch at the wall to rob the Rays’ Gabe Kapler of a home run, preserving Mark Buehrle’s perfect game. Watch footage from the game below:

11. Phantom Goal
June 9, 2010
In sudden-death overtime of the sixth game of the NHL championship series, Patrick Kane sent a stealthy shot past Philadelphia goalie Michael Leighton, winning the Stanley Cup for the Blackhawks. Kane immediately dropped his gloves and celebrated—though the shot had been so elusive not everyone realized that the game was over. (Official reviews confirmed the puck had indeed gone in.) That riveting play was the perfect way to punctuate the franchise’s renaissance—and its first Stanley Cup in 49 years. Watch Kane make the game-winning shot in the video below:

10. Panic Button
September 22, 1959
After the White Sox beat the Cleveland Indians to clinch the 1959 American League pennant, Chicago’s fire commissioner, Robert J. Quinn, set off the city’s air raid sirens. Hysterical non-Sox fans took to the streets, convinced that World War III was about to begin.

9. Twilight Zone
September 28, 1938
With night closing in on Wrigley Field, the umpires were ready to call the Cubs’ game against the first-place Pittsburgh Pirates because of darkness, ending it in a tie. But with two outs in the bottom of the ninth, Cubs catcher Gabby Hartnett swung and connected on an 0–2 pitch, belting a game-winning homer into the left-center-field gloom. A mob of delirious players and fans circled the bases with Hartnett, whose “homer in the gloamin’” put the Cubs in first place to stay—and remains the most dramatic hit in Cubs history.

8. Storybook Beginning
June 12, 1991
The best era in Chicago sports began when the Bulls won their first championship, beating the Los Angeles Lakers 108–101 in Game 5 of the 1991 NBA finals. Five more championships would follow. For Michael Jordan, it was an emphatic rebuke to critics who had sniped that he was too selfish, too much of a showboat, to win it all. In the visitors’ locker room after the game, with his father at his side, Jordan broke down as he clutched the championship trophy, his tears an outpouring of joy, relief, and vindication. For a great retrospective on Game 5, watch the video below:

7. Buzzer Beater
March 23, 1963
At Freedom Hall in Louisville, Kentucky, Loyola’s Vic Rouse tipped in an errant Les Hunter jumper with one second left in overtime to give the Ramblers a 60–58 victory—and an NCAA basketball title—over the two-time defending champion Cincinnati Bearcats. For footage from the Loyola game, watch the video below:

6. Overtime Marathon
April 10, 1934
The Blackhawks and Detroit Red Wings were locked in an epic stalemate to claim the 1934 Stanley Cup, playing three periods and two overtimes without scoring a goal. Then the Blackhawks’ Harold “Mush” March shot from 20 feet out and scored. Immediately, the 140-pound March (a “shrimp of a hockey player,” according to one newspaper account) patted Detroit goalie Wilfrid Cude on the back in sympathy and dove into the net, grabbing the puck for a souvenir. More important, the Blackhawks had won their first Stanley Cup.

5. Down to a T
December 8, 1940
In the NFL championship game of 1940, the Bears were itching for revenge against the trash-talking Washington Redskins, whose owner had called the Bears “crybabies” after his team had beaten them a few weeks earlier. On the second play from scrimmage, using the T formation they had perfected that season, the Bears scored on a 68-yard run by Bill Osmanski—a taste of the carnage to come. By the time it was over, the Bears had their revenge, 73–0, the most lopsided trouncing in NFL history. After this game, most pro teams rushed to adopt the potent T formation, and the modern era of football was born.

4. Solo Series Shot
October 23, 2005
With Game 2 of the White Sox–Astros World Series tied 6–6 in the bottom of the ninth, Sox outfielder Scott Podsednik, who had not hit a home run during the regular season, launched a Brad Lidge fastball into the right-field stands. The Sox were on their way to a sweep—and the city’s first baseball championship since 1917.

3. The Shot
May 7, 1989
Heading into the first round of the 1989 playoffs, the Cleveland Cavaliers were considered one of the best teams in the NBA, and the Bulls a good team with a great player. But everything changed in the deciding Game 5. With three seconds to go and the Bulls down by one, Michael Jordan nailed a double-pump 15-footer over Craig Ehlo. Jordan’s celebration was almost as good as the shot: leaping, punching the air with his fist, and yelling, “Go home!” to Cleveland’s fans. The Bulls failed to reach the NBA finals that year—losing to the thuggish Detroit Pistons in the conference finals—but “the shot” announced that their time was coming. Watch Michael's game-winner—and his reaction—in the video below:

2. The Long Count
September 22, 1927
In the seventh round of the most ballyhooed fight of the Jazz Age, 105,000 spectators at Soldier Field watched Jack Dempsey stagger Gene Tunney with a thunderous left hook, then drop him to the canvas with a flurry of blows. But Dempsey failed to retreat to the farthest neutral corner, as the rules required, and the referee delayed the start of his count. That bought Tunney crucial extra time to recover, and he went on to win what came to be known as the “battle of the long count”—one of the most controversial bouts in boxing history.

1. The Finale
June 14, 1998
In a career packed with big shots in gut-check moments, Michael Jordan conjured up a grand finale. His last shot as a Bull was a game-winning 17-foot jumper, after which he held his follow-through for an extra beat, his arm extended like an exclamation point. The shot defeated the Utah Jazz, gave Chicago its sixth NBA title and second three-peat, and proved Jordan could do just about anything—even arrange the perfect goodbye. Watch video of his final shot below: