I see quite a few Hugo + Montana decks in DT recently, and it's so annoying! It's also kind of boring, and I only have a chance if I also get Hugo in my hand (playing Hugo + Junkz). So here's the thing, when I play Piranas, I can beat Montana on occasion, but I don't do so well versus Uppers as with my Junkz deck ... what do I do?
I'd say give your deck a few more tries. With more experience, you'll get better at reading opposing opens (esp. with Edd and Jackie) and your odds of winning improve markedly. It takes me several runs with a deck before I really feel comfortable with it and have seen enough variety in opposing hands to make reliable moves.
Well Jackie is beast in Dt's and it is very hard to beat Uppers in DTs as well because of their very strong bonus and some great cards. Of course you'll see Hugtana because 18 attack difference is quite good. And montana is a very strong clan.
I'd say that Montana could get you a win in a DT but I never actually won a DT. So as FIF said, keep trying, learn the techniques with your deck or post it here get suggestions. I dunno but everything will help.