The first stage of the USA Grand Slam is the Chicago Match Cup, held at the Chicago Yacht Club from 12th–14th August. Seven teams from the USA and around the world will be competing in Tom 28 class keelboats.

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 Overall placings 
1. USA Chris Poole
2. NZL Cole Tapper
3. FRA Jean-Baptiste Bernaz
4. USA Peter Holz
5. NZL Megan Thomson
6. NZL Robbie McCutcheon
7. IRL Ruairi Finnegan
Final 1 2 3 4 5 W
Cole Tapper Cole Tapper, NZL 0 1 -1 0 0
Chris Poole Chris Poole, USA 1 0 1 1 3
Petit Final 1 2 3 W
Jean-Baptiste Bernaz Jean-Baptiste Bernaz, FRA 1 1 2
Peter Holz Peter Holz, USA 0 0 0
Semi Final 1 1 2 3 4 5 W
Jean-Baptiste Bernaz Jean-Baptiste Bernaz, FRA 0 0 0 0
Chris Poole Chris Poole, USA 1 1 1 3
Semi Final 2 1 2 3 4 5 W
Peter Holz Peter Holz, USA 0 1 0 0 1
Cole Tapper Cole Tapper, NZL 1 0 1 1 3
5th to 7th RR RM MT RF W %
Robbie McCutcheon Robbie McCutcheon, NZL 0 1 1 50%
Megan Thomson Megan Thomson, NZL 1 1 2 100%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 0%
Overall positions after Double Round Robin
1. FRA Jean-Baptiste Bern 11–1 92%
2. USA Peter Holz 9–3 75%
3. NZL Cole Tapper 7–5 58%
4. USA Chris Poole 7–5 58%
5. NZL Robbie McCutcheon 5–7 42%
6. NZL Megan Thomson 2–10 17%
7. IRL Ruairi Finnegan 1–11 8%
Round Robin 2 CP PH JB RM MT CT RF W %
Chris Poole Chris Poole, USA 0 0 1 1 0 1 3 50%
Peter Holz Peter Holz, USA 1 1 1 1 0 1 5 83%
Jean-Baptiste Bernaz Jean-Baptiste Bernaz, FRA 1 0 1 1 1 1 5 83%
Robbie McCutcheon Robbie McCutcheon, NZL 0 0 0 1 0 1 2 33%
Megan Thomson Megan Thomson, NZL 0 0 0 0 0 1 1 17%
Cole Tapper Cole Tapper, NZL 1 1 0 1 1 1 5 83%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 0 0 0 0 0%
Round Robin 1 CP PH JB RM MT CT RF W %
Chris Poole Chris Poole, USA 0 0 1 1 1 1 4 67%
Peter Holz Peter Holz, USA 1 0 0 1 1 1 4 67%
Jean-Baptiste Bernaz Jean-Baptiste Bernaz, FRA 1 1 1 1 1 1 6 100%
Robbie McCutcheon Robbie McCutcheon, NZL 0 1 0 1 0 1 3 50%
Megan Thomson Megan Thomson, NZL 0 0 0 0 1 0 1 17%
Cole Tapper Cole Tapper, NZL 0 0 0 1 0 1 2 33%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 0 1 0 1 17%