I distinctly remember that Wing Commander had "good guys" not winning paths. My second most frustrating experience in that game was intentionally choosing that path and managing to succeed on the final mission after umpteen tries (you have a crappy ship and overwhelming odds), only to have the landing autopilot fly me into the side of the Tiger's Claw. RIP.
The most frustrating part was getting halfway through the campaign, only to discover that disk 10 was corrupt. I had to send away for a new one, which was a bit of a process because companies at the time were loathe to give additional physical media to avoid piracy. It took about 3 months to finally get the new disk.