2016 Week 8 Jaguars vs. Titans. Never a less desirable matchup, but I put up $1500 on Tennessee to cover because it was all promotional credit on Bovada and I didn't know I could convert it to actual money by sacrificing the original $100 bonus that I had already double-up several times. I thought I was playing with essentially play money at the time.
I was able to pay for our honeymoon because of that game
The Cowboys haven't beaten anybody worth a damn, either