The USA Grand Slam returns in 2021, first up is the Chicago Match Cup at the Chicago Yacht Club from 6th–8th August. Six teams from the USA and around the world will be competing in Tom 28 class keelboats.

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 Overall placings 
1. NZL Alastair Gifford
2. USA Peter Holz
3. USA Steven Lowery
4. USA Chris Poole
5. IRL Ruairi Finnegan
6. USA Peter Bailey
Final 1 2 3 4 5 W
Alastair Gifford Alastair Gifford, NZL 0 1 1 1 3
Peter Holz Peter Holz, USA 1 0 0 0 1
Petit Final 1 2 3 W
Chris Poole Chris Poole, USA 0 0 0
Steven Lowery Steven Lowery, USA 1 1 2
Semi Final 1 1 2 3 4 5 W
Alastair Gifford Alastair Gifford, NZL 1 0 1 1 3
Steven Lowery Steven Lowery, USA 0 1 0 0 1
Semi Final 2 1 2 3 4 5 W
Peter Holz Peter Holz, USA 1 1 0 0 1 3
Chris Poole Chris Poole, USA 0 0 1 1 0 2
5th / 6th 1 2 3 W
Ruairi Finnegan Ruairi Finnegan, IRL 1 0 1 2
Peter Bailey Peter Bailey, USA 0 1 0 1
Round Robin 2 CP PH AG SL RF PB W %
Chris Poole Chris Poole, USA 0 1 0 1 1 3 60%
Peter Holz Peter Holz, USA 1 0 1 1 0 3 60%
Alastair Gifford Alastair Gifford, NZL 0 1 0 1 1 3 60%
Steven Lowery Steven Lowery, USA 1 0 1 0 0 2 40%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 1 0 1 20%
Peter Bailey Peter Bailey, USA 0 1 0 1 1 3 60%
Round Robin 1 CP PH AG SL RF PB W %
Chris Poole Chris Poole, USA 0 -0.5 0 1 1 1.5 30%
Peter Holz Peter Holz, USA 1 0 1 1 0 3 60%
Alastair Gifford Alastair Gifford, NZL 1 1 1 1 1 5 100%
Steven Lowery Steven Lowery, USA 1 0 0 1 1 3 60%
Ruairi Finnegan Ruairi Finnegan, IRL 0 0 0 0 0 0 0%
Peter Bailey Peter Bailey, USA 0 1 0 0 1 2 40%