Nobody around the NBA expected the Chicago Bulls to be anything special this season, but few anticipated things getting this ugly this quickly.

Take one of the youngest rosters in the league, throw in a brand-new coaching staff and pair it with one of the toughest schedules to start the season and you've got a recipe for disaster.

The Bulls sit at 1-8 through their first nine games, with their lone victory coming against the Milwaukee Bucks, who have also managed just one win this season.

Unfortunately for Chicago, the schedule isn't getting much easier. The Bulls will face the Spurs, Hawks, Timberwolves, Cavaliers and Nets over their next five games.

So, when will the Bulls finally pick up win No. 2?

Win Probability: 5%

Let's get the toughest matchup out of the way first.

The Spurs are one of the best teams in basketball and Victor Wembanyama is putting up numbers that look like something straight out of Wilt Chamberlain's stat sheet. The French superstar is coming off a ridiculous 40-point, 11-rebound and eight-block performance in just 27 minutes.

Chicago has been getting bullied in the paint all season, and Wembanyama might be the worst possible matchup for this frontcourt.

Things don't get much easier on the perimeter, either. San Antonio's three-headed monster of De'Aaron Fox, Stephon Castle and Dylan Harper presents another nightmare for a Bulls defense that has struggled to contain opposing ball handlers.

Unless Chicago catches fire from three, this one could get ugly quickly.

Win Probability: 40%

Now we're talking.

The Hawks are off to a strong 7-5 start and currently sit fourth in the Eastern Conference. Nickeil Alexander-Walker has carried his breakout play from last season into this year, while Jalen Johnson continues to establish himself as one of the conference's most talented forwards.

Atlanta's offseason additions have provided much-needed shooting and defense, making this a significantly more balanced team.

Still, the Hawks aren't unbeatable.

Chicago has a history of playing Atlanta tough, and with the home crowd behind them, the Bulls should have an opportunity to keep this one competitive.

If Josh Giddey can control the tempo and Chicago gets some production from its shooters, an upset isn't out of the question.

Win Probability: 11%

Anthony Edwards has been sidelined with an injury, but Minnesota hasn't missed a beat.

Since acquiring LaMelo Ball, the Timberwolves have established themselves as one of the league's most dangerous teams. Former Bull and Chicago native Ayo Dosunmu has also stepped up in Edwards' absence, providing valuable production in the backcourt.

Minnesota's combination of athletic guards and Rudy Gobert protecting the rim is another brutal matchup for Chicago.

The Bulls have struggled to defend the perimeter and finish possessions defensively, two weaknesses the Timberwolves are more than capable of exploiting.

A win here would be one of the biggest surprises of Chicago's young season.

Win Probability: 31%

The Cavaliers have been one of the more disappointing teams to start the season.

Cleveland largely brought back the same core from last year, with former Nuggets forward Peyton Watson serving as its biggest offseason addition. Despite that continuity, the Cavaliers have struggled to find their rhythm and currently sit below .500.

That doesn't mean the Bulls should expect an easy game.

Cleveland still has one of the most talented rosters in the Eastern Conference, and Donovan Mitchell always seems to save some of his best performances for Chicago.

The Cavaliers might have their issues when the playoffs roll around, but they're far too talented to keep struggling throughout the regular season.

Still, if Cleveland's early-season struggles continue, Chicago could have an opportunity to steal this one.

Win Probability: 57%

Finally, a matchup Bulls fans can actually feel good about.

Despite acquiring Julius Randle during the offseason, the Nets have joined Chicago near the bottom of the Eastern Conference standings.

Michael Porter Jr. continues to produce at a high level, while rookie Mikel Brown Jr. has started finding his footing. Still, Brooklyn lacks the overall balance and depth to consistently compete with better teams.

And yes, despite their 1-8 record, the Bulls should be the better team in this matchup.

Chicago will need Josh Giddey to be aggressive offensively, Caleb Wilson to continue his impressive rookie campaign and, perhaps most importantly, somebody to actually knock down some three-pointers.

Even on the road, this is a game the Bulls should be capable of winning.

November 18th against Brooklyn is Chicago's best opportunity to pick up its second win of the season.

The Hawks and Cavaliers games offer some upset potential, but expecting the Bulls to beat San Antonio or Minnesota would be asking an awful lot from a team that has struggled just to stay competitive.

Of course, there's always the possibility that Chicago catches fire from beyond the arc and steals a game nobody expects it to win.

But given what we've seen through nine games, Bulls fans might have to endure another difficult week before finally celebrating win No. 2.