You need software with historic option price data for this, eg. ONE (Option Net Explorer). In this you can simulate any trade in the past, choosing enter and exit points (even in 5 minute intervalls).
So lets say you establish a specific rule for a trade eg. buy AAPL straddle 5 days before earning announcement. You go back in time, enter the trade and then you forward in time and see what happens. You choose when to exit and the tool tracks performance. You do this for 8 quarters in the past and check total performance to see if this is a high probability trade or not...
Hope it helps