OLD:
private string Check_long(string input)
{
    input = input.Replace("cool", "supercool");
    input = input.Replace("cool1", "supercool1");
    input = input.Replace("cool2", "supercool2");
    input = input.Replace("cool3", "supercool3");
    return input;
}
NEW:
private string Check_short(string input)
{    
    input = Regex.Replace(input, "cool", "supercool", RegexOptions.IgnoreCase);
    input = Regex.Replace(input, "cool1", "supercool1", RegexOptions.IgnoreCase);
    input = Regex.Replace(input, "cool2", "supercool2", RegexOptions.IgnoreCase);
    input = Regex.Replace(input, "cool3", "supercool3", RegexOptions.IgnoreCase);
    return input;
}
The old solution with String.Replace was working just fine. But it didn't support case-insensitivity. So I had to check for Regex.Replace, but now it won't work. Why is that ?
Your new code should work fine. Note that you can also retain the case of your input using a capture group:
private string Check_short(string input)
{    
    return Regex.Replace(input, "(cool)", "super$1", RegexOptions.IgnoreCase);
}
                        working fine here:
        string input = "iiii9";
        input = Regex.Replace(input, "IIII[0-9]", "jjjj" , RegexOptions.IgnoreCase);
        label1.Text = input;
output
jjjj
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