I think there are broadly two types of ways to lose in a war.
The first way is that you've been to articulate clear goals, have been able to string together methods and means that at least on paper allow you to reach those goals, have been able to secure the relevant support (so national/popular will, backing of an aristocratic class, etc etc) to see through the task, and then come up short. For a classic example of this, we can look at WW1 Germany. Despite everything we know about how the war ended up, there was a path (but treacherous) to the Central Powers achieving their goals and being able to set the terms at the end of the war.
The second level is that you've failed one or more of the above tasks. In which case you're likelihood is losing gets much higher, possibly to the point where future historians might look back and say that you've lost before you even started. For classic examples of this, you would look at WW2 Japan and Pearl Harbor. It is incredibly difficult to find any analysis that didn't require continuous strings of miracles for Japan to achieve its aims once it had attacked the United States. Note that the second case consists mostly of a lot of "non-military" things.
Another thing that may help you out in your quest is to grasp of some of those is to understanding the three tier organization of tactics, operations and strategy. In fact, I can point you right back to one the author's blog series (this is part one of a six part series) where he analyzes the siege of gondor (yes LOTR) from a realistic-ish point of view (https://acoup.blog/2019/05/10/collections-the-siege-of-gondo...).
It'll probably start to give you a feel for maybe how you could rephrase your original question into forms that'll more likely give you the types of answers that you'd be satisfied with.
The first way is that you've been to articulate clear goals, have been able to string together methods and means that at least on paper allow you to reach those goals, have been able to secure the relevant support (so national/popular will, backing of an aristocratic class, etc etc) to see through the task, and then come up short. For a classic example of this, we can look at WW1 Germany. Despite everything we know about how the war ended up, there was a path (but treacherous) to the Central Powers achieving their goals and being able to set the terms at the end of the war.
The second level is that you've failed one or more of the above tasks. In which case you're likelihood is losing gets much higher, possibly to the point where future historians might look back and say that you've lost before you even started. For classic examples of this, you would look at WW2 Japan and Pearl Harbor. It is incredibly difficult to find any analysis that didn't require continuous strings of miracles for Japan to achieve its aims once it had attacked the United States. Note that the second case consists mostly of a lot of "non-military" things.
Another thing that may help you out in your quest is to grasp of some of those is to understanding the three tier organization of tactics, operations and strategy. In fact, I can point you right back to one the author's blog series (this is part one of a six part series) where he analyzes the siege of gondor (yes LOTR) from a realistic-ish point of view (https://acoup.blog/2019/05/10/collections-the-siege-of-gondo...).
It'll probably start to give you a feel for maybe how you could rephrase your original question into forms that'll more likely give you the types of answers that you'd be satisfied with.