Hmmm, I love hypothetical battles between fictional characters, hehe! Sooo Ashton at first is usually quiet, he doen't like to be noticed or bothered, and he's pretty suspicious if someone starts being nice to him or overly friendly so he probably wouldn't take to Strade in the bar. Ashton is much taller and heavier than Strade by a large amount I think, plus Ash, while not a great fighter, is pretty strong when he gets mad, plus he has high endurance, so Strade wouldn't be able to subdue him after the bar (unless Ash was drugged).
IF Strade managed to get Ash into the basement, Strade would probably get bored because Ash would be able to resist a lot of the pain, and Strade seems to like when he can break down his victims, but by that point I'm confident my smart baby boi Ash could overpower and outsmart Strade. Also, if Ash is still self aware that he's still technically in a "game", he'd hack himself out of the situation as soon as he got to his phone or even Strade's computer♫