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Round 1: TCW Season 5 Kenobi

Round 2: ROTS Obi Wan Kenobi

Battle takes place on neutral ground

*Lightsabers only

TCW Kenobi loses. ROTS Kenobi could probably keep up with Grievous's assault although he wouldn't be landing any FOrce blasts on the General.

Round 1: loses 10/10
Round 2: loses 9/10

Well ROTS was part of Legends, so technically ROTS Kenobi already beat Legends Grievous.

RotS Obi-Wan should still win.

TCW, nah.