16 Drivers. 8 Battles. 1 Urban Gauntlet.
The Mid-Season Madness Tournament heads to the concrete jungle of Chicago for Round 3. The walls are ready to punish the slightest mistake. Precision is at a premium. This week’s battles could produce the most dramatic upsets yet. A single missed braking point could be the difference between advancing and ending your tournament run in a tire barrier.
Let’s break down the eight head-to-head match ups as 16 drivers fight for survival on the streets of Chicago.
🧨Match ups and Street Course Story lines
🏁 #1 Jason Landry vs #17 Steven Neal
Landry enters as the odds-on favorite. On a technical street circuit like Chicago, his road course mastery could be untouchable. Still, street courses can level the playing field. If Neal can keep it clean, there’s a sliver of hope. He must also capitalize on any mistake.
Prediction: Landry uses precision to advance, unless disaster strikes.
🌀 #8 Jax Duval vs #9 Nick Mills
This tight seeding match up should be a banger — if Duval shows up. Rumors swirl that he might miss the round entirely, joking that “he can’t turn right.” On a course filled with right-hand corners, that joke hits different. If he doesn’t grid, Mills moves on without turning a lap.
Prediction: If Duval races, it’s tight. If not, Mills advances by default.
🔨 #4 Brandon Shelton vs #20 Thomas Fox
Fox has been the underdog story of the top bracket. However, Chicago’s street course is brutal and technical. It’s a playground for drivers like Shelton who thrive under pressure. Expect Shelton to run clean and capitalize on any error Fox makes.
Prediction: Shelton by survival. Expect at least one heart-stopping wall brush.
❌ #5 Jared Kelly vs #21 Matt Schofield
Unfortunately, Kelly is out this week due to a family obligation, giving Matt Schofield a clear path to Round 4. It’s not the preferred way for any driver to advance. But in a tournament this intense, you take the wins however they come.
Prediction: Schofield advances by forfeit.
⚔️ #2 David Medina Sr. vs #18 Ricky Mandella
Medina has been nearly flawless so far and may thrive on the tight, twitchy demands of a street circuit. Mandella is feisty, but he’ll need a perfect drive and a touch of chaos to overcome the 2-seed.
Prediction: Medina remains steady and focused to move on.
🧠 #7 Kevin Kyle vs #10 Chris Smorol
This one is juicy. Kyle and Smorol both have street course experience and solid racecraft. With concrete walls everywhere, this could be less about pace and more about mental control and mistake management. Expect a war of attrition — and possibly the race of the round.
Prediction: Could go either way — but whoever keeps it off the walls wins.
💥 #3 David Owens vs #14 Jose Medina
Owens is known for being clean and quick — perfect for street racing. Jose Medina’s path to victory likely relies on pushing Owens into an error. At Chicago, even a small mistake is race-ending. Medina needs to force the issue early.
Prediction: Owens squeaks by — but Medina will make him earn it.
🐺 #6 Kyle Lynott vs #22 Brandon Finley
Finley’s Cinderella run continues, but this track might be a dream killer. Lynott is smart, smooth, and brutal in elimination formats — a bad combo for a lower seed. If Finley survives lap one, it’s game on. But Lynott has the edge in discipline.
Prediction: Lynott eliminates the bracket buster — but keep an eye on lap 1.
🚧 Bonus Chaos: Street Course X-Factors
- Wall taps that bend suspensions
- Divebombs gone wrong
- Pit entry mistakes
- Lap traffic trouble
Chicago doesn’t just test speed — it tests nerves. The round’s outcome could come down to who adapts to urban warfare the fastest.
🔮 Looking Ahead
Jared Kelly is out. Jax Duval’s status is uncertain. The Chicago Street Course is ready to bite. Round 3 might be the most chaotic round of the entire bracket. 16 drivers enter, but only 8 escape the streets unscathed.
Will the favorites survive? Will the walls claim more victims? We’ll find out under the shadows of skyscrapers this weekend.
Editor’s Note:
This post was written with the assistance of ChatGPT, an AI tool that helps organize race data, shape storylines, and streamline weekly recaps. I spend time proof reading and working story lines into content. Please enjoy!
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