The code below demonstrates one way of splitting strings and then concatenating them. I misunderstood the question at first. :)
string left = string.Format("Win{0}Lose{0}Hello{0}Goodbye", Environment.NewLine);
string right = string.Format("One{0}Two{0}Three{0}Four", Environment.NewLine);
string[] leftSplit = left.Split(new[] { Environment.NewLine }, StringSplitOptions.None);
string[] rightSplit = right.Split(new[] { Environment.NewLine }, StringSplitOptions.None);
string output = "";
if (leftSplit.Length == rightSplit.Length)
{
for (int i = 0; i < leftSplit.Length; i++)
{
output += leftSplit[i] + ":" + rightSplit[i] + Environment.NewLine;
}
}