| Date/Time | Matchup | Prediction | Actual | Result |
|---|---|---|---|---|
| 5/17/2025 |  Chicago Sky @ Indiana Fever  by 8 | Indiana Fever win 87.7-86.2 won 54.76% of sims, average margin of 1.6 | Indiana Fever wins 93-58 |  |
| 5/22/2025 |  New York Liberty @ Chicago Sky by 11 | Chicago Sky win 88.3-85.5 won 57.75% of sims, average margin of 2.8 | New York Liberty wins 99-74 |  |
| 5/25/2025 | Chicago Sky @ Los Angeles Sparks  by 5 | Los Angeles Sparks win 69.5-52.6 won 88.88% of sims, average margin of 16.9 | Los Angeles Sparks wins 91-78 |   |
| 5/26/2025 6:15:01 PM | Chicago Sky @ Phoenix Mercury  | Simulate | | |
| 5/27/2025 | Chicago Sky @ Phoenix Mercury by 7 | Phoenix Mercury win 56.8-40.7 won 90.70% of sims, average margin of 16.2 | Phoenix Mercury wins 94-89 | |
| 5/29/2025 |  Dallas Wings @ Chicago Sky by 1 | Dallas Wings win 59.1-45.7 won 85.24% of sims, average margin of 13.4 | Chicago Sky wins 97-92 | |
| 5/31/2025 | Chicago Sky @ Dallas Wings by 2 | Dallas Wings win 84.9-74.1 won 78.25% of sims, average margin of 10.8 | Chicago Sky wins 94-83 | |
| 6/7/2025 | Indiana Fever @ Chicago Sky by 3 | Indiana Fever win 78.6-78.0 won 52.63% of sims, average margin of 0.6 | Indiana Fever wins 79-52 | |
| 6/10/2025 | Chicago Sky @ New York Liberty by 17 | New York Liberty win 92.8-74.0 won 91.74% of sims, average margin of 18.8 | New York Liberty wins 85-66 | |
| 6/12/2025 6:15:01 PM | Chicago Sky @ Atlanta Dream  | Simulate | | |
| 6/13/2025 | Chicago Sky @ Atlanta Dream by 12 | Atlanta Dream win 84.3-70.6 won 83.13% of sims, average margin of 13.8 | Atlanta Dream wins 88-70 | |
| 6/15/2025 | Chicago Sky @ Connecticut Sun  by 1 | Chicago Sky win 77.8-72.8 won 64.25% of sims, average margin of 5.0 | Chicago Sky wins 78-66 | |
| 6/17/2025 |  Washington Mystics @ Chicago Sky by 4 | Washington Mystics win 77.7-72.9 won 63.38% of sims, average margin of 4.8 | Washington Mystics wins 79-72 | |
| 6/21/2025 | Phoenix Mercury @ Chicago Sky by 11 | Phoenix Mercury win 81.2-72.6 won 71.00% of sims, average margin of 8.6 | Phoenix Mercury wins 107-86 | |
| 6/22/2025 | Chicago Sky @ Atlanta Dream by 16 | Atlanta Dream win 85.6-67.9 won 89.00% of sims, average margin of 17.7 | Atlanta Dream wins 93-80 | |
| 6/23/2025 6:15 PM | Los Angeles Sparks @ Chicago Sky | Simulate | | |
| 6/24/2025 | Los Angeles Sparks @ Chicago Sky by 5 | Chicago Sky win 76.9-73.7 won 56.63% of sims, average margin of 3.1 | Chicago Sky wins 97-86 | |
| 6/27/2025 | Chicago Sky @ Golden State Valkyries  by 8 | Golden State Valkyries win 85.2-76.7 won 70.63% of sims, average margin of 8.5 | Golden State Valkyries wins 83-78 | |
| 6/29/2025 | Chicago Sky @ Los Angeles Sparks by 8 | Los Angeles Sparks win 81.3-72.7 won 72.50% of sims, average margin of 8.5 | Chicago Sky wins 92-85 | |
| 7/6/2025 | Chicago Sky @ Minnesota Lynx  by 14 | Minnesota Lynx win 89.6-73.3 won 87.63% of sims, average margin of 16.3 | Minnesota Lynx wins 80-75 | |
| 7/8/2025 | Chicago Sky @ Washington Mystics by 6 | Washington Mystics win 77.4-73.7 won 61.75% of sims, average margin of 3.7 | Washington Mystics wins 81-79 | |
| 7/9/2025 | Dallas Wings @ Chicago Sky by 1 | Chicago Sky win 82.7-79.4 won 61.25% of sims, average margin of 3.3 Projected Stats  | Chicago Sky wins 87-76 | |
| 7/12/2025 | Minnesota Lynx @ Chicago Sky | Minnesota Lynx win 92.1-87.6 won 70.00% of sims, average margin of 4.5 | | |
| 7/14/2025 | Minnesota Lynx @ Chicago Sky | Minnesota Lynx win 86.2-77.3 won 80.00% of sims, average margin of 8.9 | | |
| 7/16/2025 | Atlanta Dream @ Chicago Sky | Simulate | | |
| 7/22/2025 | Chicago Sky @ Minnesota Lynx | Simulate | | |
| 7/24/2025 |  Seattle Storm @ Chicago Sky | Simulate | | |
| 7/27/2025 | Indiana Fever @ Chicago Sky | Simulate | | |
| 7/29/2025 | Chicago Sky @ Washington Mystics | Simulate | | |
| 8/1/2025 | Golden State Valkyries @ Chicago Sky | Simulate | | |
| 8/3/2025 | Phoenix Mercury @ Chicago Sky | Simulate | | |
| 8/5/2025 | Washington Mystics @ Chicago Sky | Simulate | | |
| 8/7/2025 | Atlanta Dream @ Chicago Sky | Simulate | | |
| 8/9/2025 | Chicago Sky @ Indiana Fever | Simulate | | |
| 8/13/2025 | Chicago Sky @ Connecticut Sun | Simulate | | |
| 8/15/2025 | Golden State Valkyries @ Chicago Sky | Simulate | | |
| 8/19/2025 | Seattle Storm @ Chicago Sky | Simulate | | |
| 8/21/2025 | Chicago Sky @ New York Liberty | Simulate | | |
| 8/23/2025 | Connecticut Sun @ Chicago Sky | Simulate | | |
| 8/25/2025 |  Las Vegas Aces @ Chicago Sky | Simulate | | |
| 8/28/2025 | Chicago Sky @ Phoenix Mercury | Simulate | | |
| 8/30/2025 | Chicago Sky @ Seattle Storm | Simulate | | |
| 8/31/2025 | Chicago Sky @ Seattle Storm | Simulate | | |
| 9/3/2025 | Connecticut Sun @ Chicago Sky | Simulate | | |
| 9/4/2025 | Connecticut Sun @ Chicago Sky | Simulate | | |
| 9/5/2025 | Chicago Sky @ Indiana Fever | Simulate | | |
| 9/7/2025 | Chicago Sky @ Las Vegas Aces | Simulate | | |
| 9/9/2025 | Chicago Sky @ Las Vegas Aces | Simulate | | |
| 9/11/2025 | New York Liberty @ Chicago Sky | Simulate | |
Legend/Totals
| Correct Picks | 15 (78.9%) |
| Incorrect Picks | 4 (21.1%) |
| Final Margin within 5 Pts | 7 (36.8%) |
| Beat the Spread | 8 (42.1%) |
