Should Cap have been able to defeat his old self easily? We know that Cap became a better fighter between Avengers and Winter Soldier (Remember Natasha's criticism of Caps fighting skills with Loki "This guys's all over the place") and so shouldn't it have been a lot easier for him to beat his inexperienced other self?
I'm not saying he was a bad fighter, just not as good as he was later. Think about it: how much time did Steve actually train with his new strength after he received it in First Avenger? He could not have been as good as Natasha at hand to hand combat, hence her criticism of his fighting skills in Avengers in the Loki fight.
However, it seems clear to me that he has been training with SHIELD and probably with Natasha by the time of Winter Soldier
Cap has the type of personality that he is always going to work hard, even though he has super powers. So I think youre right because he would have been training very hard plus he had top people to train with like Nat.
I would say it’s likely older Cap held back against 2012 Cap. That’s what it looked like to me. And why wouldn’t he? Unlike younger Cap, older Cap knew exactly who he was facing — and I kinda doubt completely kicking his younger self’s ass is what he was gonna try to do.