Sonic Prime, but only Shadow (and Sonic) fights with Grim Sonic and its duplicates. 

Grim Sonic is a formidable opponent, even Shadow, the ultimate lifeform, cannot easily defeat him easily. Here are all the scenes that Shadow (& Sonic) faces Grim Sonic.
00:00 Shadow and Sonic faces Grim Sonic for the first time
01:35 Grim Sonic gets back
01:47 Shadow's defeat 1
02:01 Shadow's return
02:46 Sonic and Shadow VS Grim Sonic's duplicates 1
03:21 Sonic and Shadow VS Grim Sonic's duplicates 2
03:26 Grim Sonic's defeat 1
03:43 You are not going anywhere
03:54 The final round
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