I think fans that aren't convinced of our ability to beat Boro are actually fairly correct in their assumptions. If supporting this club has taught me anything in the last decade or so, it's that if something can go wrong, it will most certainly go wrong, as well as that we don't really deserve good things. I am actually convinced we're going to beat Boro, but I'm not convinced we're going to get to the CL group stage, I find it very easy to picture us losing the qualifier.
This club has a tendency of "forcing" magic moments, ever since Istanbul there's this forceful "no, this is meant to be so it better be so" feeling around it, and media cater to that feeling too, you could see it in our title challenge all the way up to the slip, sure that season felt nice, but the cringe on the pitch and interviews was way too much to take, the film speech of how this will not slip, the slip, the sheer arrogance of thinking Palace are going to roll over and we're gonna boost our GD by rapidly scoring past them like it's a bad FIFA game... this forcing of magic is really counter-productive, and yet the club keeps doing it and as a result I think players and managers also think it's meant to be and it's their destiny to win, so they don't try or underestimate the opponent's strength.
Not to mention underestimating teams is a weakness on its own too, you can see it when we're playing bad teams at home and draw/lose.
We do tend to have tons of bad luck on our "way back to the top" (which has been going on for the past 6 years at least), last year we've been in the same finals United were in this year, and yet failed to win any of them. On the other hand, I am completely convinced United are winning the EL, while we had to struggle against super teams like Borussia and Sevilla, they had the easy run of playing second-tier Benelux teams.
Every single team that's been on a losing streak, managed to beat us. Sunderland, Hull, Palace, Swansea, Bournemouth took 5pts off us. Same teams would then go on and painfully lose to average opposition next week. It kept happening all season. Not to mention how Bournemouth game was a typical "magic of the FA cup" shit fest where a goal doesn't count because the ball is few millimeters too close to the line, and then the other team breaks your team's morale and humiliates you with set-piece goals. Can't wait to visit that shit ground next season again, how they're able to have stands with loud as feck fans so close to the pitch without breaking any rules, I have no idea. How some morbidly obese midget that will never achieve anything in his life can then come on and outrun all of your defenders and become a scottish messi in a matter of minutes, is also beyond me.
Last season UEFA managed to suspend our best performing defender for drugs, then next season, after we've already played and lost a European final without him, they "suddenly realised" he didn't take anything illegal. This season Matip retired from international football, yet was forbidden from playing for the club for some reason, again a "weird" "coincidence". And my favourite instance of utter failure was how the great four of Lallana, Mane, Phil and Bob were constantly injured and never actually played together after being promoted as the most attacking group in England.
All in all, we tend to have bad luck and we tend to fail way too much for comfort, so i won't be surprised if we fail against Boro or in the qualifier. If we do, I'm sure the fans will once again pretend like it's all fine and dandy, like they always do when Klopp comes out with an excuse. He's an extremely lovable guy, and it's hard to even think of letting him go, ever. His persona somehow makes him get away with a lot of real humiliating shit on the pitch, but whatever, optimism also has its place in the game, let's just see if we can beat Boro and take it from there.
But let me also be clear that it's one thing if you make piles of shite like Forster, Heaton and Fabianski look like world class goalkeepers, but if this team manages to make Guzan look like even a decent goalkeeper, I'll probably off myself.