Who has settled disputes in court, and won economically?

I feel like the answers to this will be heavily skewed by the jurisdiction you live under.

Here in the UK, I had an airline hold a substantial amount of my money hostage and they refused to engage in a discussion to allow me to get my money back. I spent ~30mins filling out a small claims court application, paid the obligatory £115 fee, and a few weeks later the airlines lawyers contacted me offering me my money back along with a decent amount of compensation.

Equally, I've witnessed people pursue employment tribunal claims against their employer here in the UK, only for the process to take years, the preparatory effort being enormous, and the outcome being a positive judgement in their favour along with an insultingly meagre financial award. For some, that's still worth it purely for the vindication and validation.

The courts rarely help. I've consulted lawyers about multiple issues over the years and gotten consultations. Each time the answer was the same - yes, this was an obvious violation of your rights and/or law, but there's not much of a case since the damages weren't severe and the system doesn't care about ADA or civil rights violations unless there was some severe injury. And yet I've seen frivolous suits with no basis make it in front of a judge.

I’ve done small claim court a few times and won. The cases were mostly rent related.

My personal belief is that once you end up in court, you're both lovers.

There would need to be significant amounts on the table before I'd start a court proceeding against a business.

I have had to use the court gor an eviction, but it took a long time, cost money, and we didn't get anything back. Even then it's a last resort - usually we just offer the tenant a pile of cash to move out. (It leaves a bad taste, but is cheaper and faster than a court eviction.) The long term solution is to pick better tenants.

In business you can't stop someone taking you to court, but you can make every effort (aka give them money) to make it go away.

You can win economically, especially if it's a slam dunk case and hence get a lawyer on contingency. That said, it can take a long time to resolve which can prolong any stress surrounding it. And even if the other party is clearly, obviously at fault, they may spread falsehoods about you and the case. Especially if this is done in private, it's practically difficult to do anything about.

Well, you should do cost analysis BEFORE you go to court. That does not mean just how much money you should get out but also whether the other side is even capable of paying.

The government itself is often a big violator, and is very difficult to sue. The judges are not going to meaningfully punish the governments.

I dealt with such case and won legally but did not win anything economically.