I'll only use Winston when I feel like he's set up to excel against a certain team. Enemy teams that rely on a Reinhardt as their main tank get eaten up by Winston. So if he's in play along with a sniper or 2 and a Genji then Winston is primed to severely disrupt their game. I don't seem to encounter any issues matching up against D.Va. She's similar to Reinhardt in that her shield can't block Winston's Tesla cannon so if you drop your barrier and shoot her through it you're doing damage and she isn't.
So far I've found the best way to use him is to either take down a lone character (like a sniper) or to jump into a group of enemies, drop the shield and try to kill someone valuable like a Mercy or Genji before jumping back out.
His ultimate doesn't seem very useful for securing kills and I have yet to knock a player off a cliff but triggering it when you're close to death is a good way to get back to full health so you can stay in the fight.
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