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So say a character with Oppress 1 attacks Topspin with Clobber as his head (Bold 3) and no other sources of Bold. How does Oppress interact with Topspin's Tough here?

The static ability of Topspin's alt mode (As well as the opposite side of Malevolent Architect) that sets their Tough equal to their Bold always applies before Oppress kicks in. Then Oppress will reduce each total by whatever the Oppress value is. So with Topspin + Clobber, Topspin will have Bold 2, and thus Tough 2 after Oppress is applied.
Source: Aequitas (2023-07-05)    【Link to Ruling】
Tags: Clobber, Topspin, Air & Space Assault, Oppress