I have read where Grant most regretted the Federal assault at Cold Harbor.
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General Grant regretted the assault on Cold Harbor during the American Civil War. He described it as an unnecessary and costly battle in which thousands of Union soldiers lost their lives. Grant later acknowledged that he should not have ordered the assault and expressed remorse for the resulting high casualties.
His first battle was won in Missouri at the battle of Vicksburg.
Grant's victory over Bearegard at Shiloh.
The rebels sprang on Grant's sleepy camp.
It was a civil war battle- Bragg v Grant. Union prevailed.