Best Underdog Moments in Chicago Sports History

Chicago’s championship banners can make its sporting history look more inevitable than it felt at the time. Before the celebrations came teams with losing records, unfavorable matchups and opponents who had every reason to expect victory.

Michael Jordan hangs in the air and Craig Ehlo lands beneath him. Someone watching the replay still clenches a fist. The ending is familiar. Cleveland’s reasons for expecting to win are easier to forget.

Put the uncertainty back into the picture and even the most replayed moments become worth another look.

Jordan Beats the Team That Had Chicago’s Number

Cleveland swept all six regular-season meetings with the Bulls in 1988-89. The Cavaliers finished 57-25, ten wins ahead of Chicago, and entered the playoffs as the Eastern Conference’s third seed. The Bulls were sixth.

On May 7, 1989, the deciding fifth game was in Cleveland. Ehlo’s layup put the Cavaliers ahead 100-99 with three seconds remaining.

Jordan took the inbound pass, moved toward the foul line and rose. Ehlo challenged him, but Jordan released the ball after his defender began descending. Chicago won 101-100. Jordan finished with 44 points.

Before he became synonymous with winning, believing in his Bulls required considerably more faith than watching the highlights does now.

Fast-forward 37 years and the Bulls have another opportunity to exceed expectations. Before the season begins, the prices give you a sense of how much Chicago still has to prove. Through online casino and sportsbook SpinBet’s sports betting nz offering, you can assess Chicago’s prospects through NBA futures and regular-season win totals, alongside game moneylines, handicaps and player props. Chicago’s championship price of +7000 puts a title among the distant possibilities. A win total of 29.5, with over priced at -105, gives you a measure of expectations across 82 games.

Whether Chicago can clear that mark depends partly on how quickly a new coach and a prized rookie find their feet. Tiago Splitter takes over on the sidelines and fourth overall pick Caleb Wilson joins a team whose front office has openly acknowledged the Bulls are rebuilding. Earning more respect over a season would be a meaningful start.

Before judging the new lineup, consider what you can watch for:

1. Whether Wilson earns consistent minutes rather than relying on occasional highlights.
2. Whether Chicago protects the ball when opponents pressure Giddey.

The White Sox Make “Hitless” Sound Ridiculous

The 1906 Cubs won 116 regular-season games. Across town, the White Sox won 93 and batted .230, the lowest average in the American League. The “Hitless Wonders” scarcely sounded like champions.

The Sox entered the World Series as 3-to-1 underdogs. Then their pitching and opportunistic offense made the gap between the clubs look smaller.

Ed Walsh struck out 12 in a 3-0 Game 3 victory. With the series tied 2-2, Chicago’s hitters scored eight runs in each of the next two games. Frank Isbell hit four doubles in Game 5. The Sox clinched with an 8-3 victory in Game 6.

An insult had become the name of a champion. Particularly satisfying coming from a Cubs supporter.

The South Side has another unexpected postseason story in 2026. The Sox swept Houston before taking a 2-1 Division Series lead over Cleveland. Their World Series market price of +1300 captured the distance still to travel. When checking baseball futures through SpinBet, you have a team’s route through the remaining rounds to consider as well as its most recent win.

The Bears Announce Themselves Before 1985

The championship Bears are remembered as intimidators. A year earlier, they went to Washington as seven-point underdogs in the divisional playoffs.

Washington had appeared in the previous two Super Bowls. Chicago had not won a postseason game since 1963 and was starting Steve Fuller in place of injured quarterback Jim McMahon.

On December 30, 1984, Richard Dent recorded three of seven sacks. Walter Payton rushed for 104 yards and threw a 19-yard touchdown pass to tight end Pat Dunsmore. Fuller found Willie Gault for a 75-yard touchdown.

Chicago won 23-19. The Bears subsequently lost the NFC Championship Game to San Francisco, but Washington had already discovered what the defense could do.

The players won without knowing a Super Bowl triumph lay ahead.

For the current Bears, a Super Bowl market price of +2000 reflects ambitions beyond an isolated upset. Comparing that outlook through SpinBet gives you a reason to examine whether Chicago can sustain its performances against stronger opponents. A memorable Sunday and a championship campaign ask different things of a team.

The Blackhawks Find a Goalie and Win a Cup

Chicago knows what a Stanley Cup parade looks like. The harder question is how far the current Blackhawks are from giving the city another one.

Chicago’s 2027 Stanley Cup market price of +22500 suggests another title would require substantial surprises. Before comparing hockey odds at SpinBet, check what the market includes: the sportsbook’s standard game-result rules use regulation time unless overtime and shootouts are specified. A team can win the game without winning a regulation-only selection.

Winning the Cup as such a long shot would demand something extraordinary. Chicago’s 1938 team managed it after winning only 14 regular-season games. Their 14-25-9 record was enough to reach the playoffs. Six of the NHL’s eight teams qualified, giving Chicago an opening unavailable under a modern format.

They beat Montreal and the New York Americans to reach the Final. Then goalie Mike Karakas broke a toe.

The club’s 2025 retrospective on its Toronto rivalry recalls Alfie Moore being summoned just hours before Game 1. His only appearance for Chicago produced a 3-1 victory over the Maple Leafs.

Karakas returned later in the series wearing a protective boot. The Blackhawks won the championship in four games.

Team and year	What Chicago had to overcome
Bulls, 1989	Six regular-season losses to Cleveland
White Sox, 1906	A Cubs opponent with 116 wins
Bears, 1984	A road playoff against the reigning NFC champions
Blackhawks, 1938	A losing record and an injured starting goalie
Sky, 2021	Two single-elimination rounds as the sixth seed

The Sky Turn a .500 Season Into a Championship

The 2021 Sky finished 16-16 and entered the playoffs as the sixth seed. Candace Parker’s return to Chicago had supplied a compelling story. It had not supplied an easy season.

Chicago survived single-elimination games against Dallas and Minnesota, then beat top-seeded Connecticut to reach the Finals.

In Game 4 against Phoenix, the Sky recovered from a 14-point deficit to win 80-74 and secure the championship. Allie Quigley scored 26 points. Kahleah Copper was named Finals MVP.

When Parker’s jersey was retired in 2025, she resisted polishing the memory. “Everybody remembers the banner, but like, we were .500,” she said in the Sun-Times account of the ceremony.

Before Anyone Knows the Ending

The banners stay up long after the doubts disappear. Parker remembered both. Chicago had reasons to hope, and plenty of reasons to worry.

The old footage gets grainier. The uniforms look stranger. Still, Cleveland has three seconds to survive, and Jordan is asking for the ball. Even now, knowing everything that followed, you hold your breath.

Gambling is for entertainment purposes only and should never be seen as a way to make money. Please gamble responsibly and only bet what you can afford to lose. 18+ only.

The post Best Underdog Moments in Chicago Sports History appeared first on ChiCitySports.

Source: https://www.chicitysports.com/best-underdog-moments-in-chicago-sports-history/