Also we should take into account that Andy was quite ill in Tokyo when he last played Milos. If he had been well would have beaten Milos so I think we can forget the H2H could be Andy leading the H2H.
I think Andy was knackered after winning the USO as well to be honest. He did have match points against Raonic, we shouldn't forget that. Personally I think he would have won if he'd been mentally fresh. I don't care though, he beat Raonic when it really mattered, at the USO. He lost to Djokovic in Shanghai last year too after having match points. To my mind the same point applies though. With all due respect to Milos and Novak, Andy got the ones that mattered.
I'm never sure how much you can read into a H2H. Andy's with Raonic could, in another situation, be in his favour. As I said, Andy could have won in Tokyo, he did have match points. Also they have a walkover each, which obviously doesn't count, but as they were on hard you could, maybe, say Andy would have been favourite to come through. Even if you credit Raonic for Tokyo, which you should, he did win, if they'd played the walkovers and Andy had won he'd be 3-2 up against Raonic, rather than 2-1 down. That would put the head to head in a different light. Some of us might still need a cushion to hide behind when they meet, (not me, I'm unflappable these days lol) but it wouldn't be so scary.
I think Andy will be fine in Madrid. I'm really looking forward to seeing him play.