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This isn't a straightforward situation. On Diamond, for example, the portal could easily be broken on turn 112. And even on X3DM1, it's not uncommon for it to be broken on the first turn, although this isn't a very likely occurrence.
Regarding the main point: I believe that the current logic of the Overlord's Hour (OH) required a replay of the Blue player's last turn, but Zee should have demanded this immediately (it seems from the stream that he immediately understood what happened and could have not waited for the results of all the previous battles). However, after Red had already moved and won 3 battles against Blue, the opportunity was lost. You formally agreed with what was happening as soon as you started moving in the first combat encounter.
If the current logic requires loading and replaying a turn, it's a flawed logic. Either we play until a rematch is decided, or we rely on the algorithm for breaking the Overlord's Hour that is built into the HD mod. Otherwise, for the sake of saving 1 hour (which is a very optimistic estimate of the time saved from the end of the rematches to the end of the Overlord's Hour), we risk creating a situation in the game where a turn is replayed, taking into account a huge amount of additional information obtained during the replayed turn.