The first stage of the 2023 USA Grand Slam is the Chicago Match Cup, held at the Chicago Yacht Club from 18th–20th August. Ten teams from the USA and around the world will be competing in Tom 28 class keelboats.

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 Overall placings 
1. FRA Timothée Rossi
2. USA Gavin Brady
3. AUS Cole Tapper
4. USA Cormac Murphy
5. USA Pearson Potts
6. USA Jeffrey Petersen
7. NZL Megan Thomson
8. GBR Matt Whitfield
9. USA Ryan Seago
10. IRL Ruairi Finnegan
Final 1 2 3 4 5 W
Timothée Rossi Timothée Rossi, FRA 0
Gavin Brady Gavin Brady, USA 0
Petit Final 1 2 3 W
Cole Tapper Cole Tapper, AUS 0
Cormac Murphy Cormac Murphy, USA 0
Semi Final 1 1 2 3 4 5 W
Timothée Rossi Timothée Rossi, FRA 1 1 1 3
Cormac Murphy Cormac Murphy, USA 0 0 0 0
Semi Final 2 1 2 3 4 5 W
Cole Tapper Cole Tapper, AUS 1 1 0 0 0 2
Gavin Brady Gavin Brady, USA 0 0 1 1 1 3
5th to 8th RR PP JP MW MT W %
Pearson Potts Pearson Potts, USA 1 1 1 3 100%
Jeffrey Petersen Jeffrey Petersen, USA 0 1 1 2 67%
Matt Whitfield Matt Whitfield, GBR -.75 0 0 -0.75 0%
Megan Thomson Megan Thomson, NZL 0 0 1 1 33%
Quarter Final 1 1 2 3 W
Timothée Rossi Timothée Rossi, FRA 1 1 2
Megan Thomson Megan Thomson, NZL 0 0 0
Quarter Final 2 1 2 3 W
Cole Tapper Cole Tapper, AUS 1 1 2
Matt Whitfield Matt Whitfield, GBR 0 0 0
Quarter Final 3 1 2 3 W
Pearson Potts Pearson Potts, USA 0 1 0 1
Cormac Murphy Cormac Murphy, USA 1 0 1 2
Quarter Final 4 1 2 3 W
Jeffrey Petersen Jeffrey Petersen, USA 0 0 0
Gavin Brady Gavin Brady, USA 1 1 2
Overall positions after Round Robin
1. FRA Timothée Rossi 9–0 100%
2. NZL Cole Tapper 7–2 78%
3. USA Pearson Potts 7–2 78%
4. USA Jeffrey Petersen 5–4 56%
5. USA Cormac Murphy 5–4 56%
6. USA Gavin Brady 4–5 44%
7. GBR Matt Whitfield 2–7 22%
8. NZL Megan Thomson 2–7 22%
9. USA Ryan Seago 2–7 22%
10. IRL Ruairi Finnegan 2–7 22%
Round Robin CM JP TR MT CT PP RF RS MW GB W %
Cormac Murphy Cormac Murphy, USA 0 0 1 1 0 1 1 1 0 5 56%
Jeffrey Petersen Jeffrey Petersen, USA 1 0 1 0 0 1 1 1 0 5 56%
Timothée Rossi Timothée Rossi, FRA 1 1 1 1 1 1 1 1 1 9 100%
Megan Thomson Megan Thomson, NZL 0 0 0 0 0 1 1 0 0 2 22%
Cole Tapper Cole Tapper, AUS 0 1 0 1 1 1 1 1 1 7 78%
Pearson Potts Pearson Potts, USA 1 1 0 1 0 1 1 1 1 7 78%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 0 0 0 0 1 1 2 22%
Ryan Seago Ryan Seago, USA 0 0 0 0 0 0 1 0 1 2 22%
Matt Whitfield Matt Whitfield, GBR 0 0 0 1 0 0 0 1 0 2 22%
Gavin Brady Gavin Brady, USA 1 1 0 1 0 0 0 0 1 4 44%