I know this post is old but my old roommate ended up losing a ton money like this.
He had a system where if he lost a sports wager, he would play roulette on his book to win back his loss by chasing.
This system worked great throughout the baseball season until one night he was chasing red on a sick black streak. The table limit was a hundred so he kept chasing after he lost his first hundred on the $1 chases. The kid eventually burned a whole season's profit within 5 minutes because he didn't stop.
Honestly that night made me convinced those online casinos are rigged because I feel like the software caught on to his system.
If you do this just change up your routines and for the love of god walk away after you lose a $100.