The Chicago Match Cup is the third stage of the 2025 USA Grand Slam, held at the Chicago Yacht Club from 15th–17th August. Nine teams from the USA and around the world will be competing in Tom 28 class keelboats.

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 Overall placings 
1. USA Peter Holz, Ian Beckley, Hector Guzman, Tim Siemers
2. USA Christian Prendergast, Sam Gilmour, Mark Spearman, Axel Munkby
3. FRA Timothée Rossi, Alice Chiappori, Armel Le Carrer, Leo Maurin, Eliott Michal
4. USA Freddie Parkin, Tomas Dietrich, Harrison Gandy, Cooper Newton, Christian Yanoti
5. FRA Tom Picot, Frank Lavenant, Robin Chantrelle, Armand Clabon, Zachary Santucci
6. USA Jack Jennings, Kieth Swinton, Payson Infelise, Alan Johnson
7. SWE Anna Östling, Annika Carlunger, Svea Sahlin, Annie Wennergren, Linnéa Wennergren
8. USA Morgan Pinckney, Peter Barnard, Addy Fisher, Peter Foley, Jimmy Prendergast
9. NZL Megan Thomson, Josi Andres, Tiana Wittey, Hattie Rogers, George Richardson
Final 1 2 3 4 5 W
Peter Holz Peter Holz, USA 1 1 2
Christian Prendergast Christian Prendergast, USA 0 0 0
Petit Final 1 2 3 W
Freddie Parkin Freddie Parkin, USA 0 1 0 1
Timothée Rossi Timothée Rossi, FRA 1 0 1 2
Semi Final 1 1 2 3 4 5 W
Peter Holz Peter Holz, USA 1 1 1 3
Freddie Parkin Freddie Parkin, USA 0 0 0 0
Semi Final 2 1 2 3 4 5 W
Christian Prendergast Christian Prendergast, USA 0 0 1 1 1 3
Timothée Rossi Timothée Rossi, FRA 1 1 0 0 0 2
5th/6th 1 2 3 W
Jack Jennings Jack Jennings, USA 1 0 0 1
Tom Picot Tom Picot, FRA 0 1 1 2
7th/8th 1 2 3 W
Morgan Pinckney Morgan Pinckney, USA 0 0 0
Anna Östling Anna Östling, SWE 1 1 2
Quarter Final 1 1 2 3 4 5 W
Peter Holz Peter Holz, USA 1 1 1 3
Morgan Pinckney Morgan Pinckney, USA 0 0 0 0
Quarter Final 2 1 2 3 4 5 W
Christian Prendergast Christian Prendergast, USA 1 1 1 3
Anna Östling Anna Östling, SWE 0 0 0 0
Quarter Final 3 1 2 3 4 5 W
Jack Jennings Jack Jennings, USA 1 0 0 0 1
Timothée Rossi Timothée Rossi, FRA 0 1 1 1 3
Quarter Final 4 1 2 3 4 5 W
Freddie Parkin Freddie Parkin, USA 0 1 0 1 1 3
Tom Picot Tom Picot, FRA 1 0 1 0 0 2
Overall positions after Round Robin
1. USA Peter Holz 7–1 88%
2. USA Christian Prendergast 6–2 75%
3. USA Jack Jennings 6–2 75%
4. USA Freddie Parkin 5–3 63%
5. FRA Tom Picot 4–4 50%
6. USA Morgan Pinckney 3–5 38%
7. SWE Anna Östling 3–5 38%
8. FRA Timothée Rossi 2–6 25%
9. NZL Megan Thomson 0–8 0%
Round Robin A� MT TR MP TP PH CP FP JJ W %
Anna Östling Anna Östling, SWE 1 1 0 0 1 0 0 0 3 38%
Megan Thomson Megan Thomson, NZL 0 0 0 0 0 0 0 0 0 0%
Timothée Rossi Timothée Rossi, FRA 0 1 0 1 0 0 0 0 2 25%
Morgan Pinckney Morgan Pinckney, USA 1 1 1 0 0 0 0 0 3 38%
Tom Picot Tom Picot, FRA 1 1 0 1 0 1 0 0 4 50%
Peter Holz Peter Holz, USA 0 1 1 1 1 1 1 1 7 88%
Christian Prendergast Christian Prendergast, USA 1 1 1 1 0 0 1 1 6 75%
Freddie Parkin Freddie Parkin, USA 1 1 1 1 1 0 0 0 5 63%
Jack Jennings Jack Jennings, USA 1 1 1 1 1 0 0 1 6 75%