|I don't think your columns lined up correctly, but I'll give it a shot anyway:|
1 - Pick a single column where you want to place Win or Lose. Let's say you start in D2.
2 - Select a bunch of cells in Column D and click on Data...Validation...Allow: List
3 - In the Source field enter:
This will create a Drop Down in each cell with your 2 choices.
4 - In E2 ,enter a formula simliar to this:
=IF(D2="Win", your formula for a Winning bet, IF(D2 = "Lose", your formula for a Losing bet, ""))
When you choose either Win or Lose, the formula will produce the result.
Drag this down as far as you have Drop Downs.
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