Deliberate mistake: When the world is counting down to the new year, we see people in various countries, Egypt, the USA etc all counting down together. Because of time zone differences this isn't possible. [It is a little joke.] (00:01:35)
Deliberate mistake: In the dorm room, Fry's punch cup appears out of nowhere. [According to the DVD commentary, this was done on purpose.]
Deliberate mistake: The fossilised dog looks like the dog did when he was young; it should look old and decrepit, as the dog was when he died. (Presumably deliberate, to avoid a spoiler.).
Answer: Yes Leela knew from early on that Fry had feelings for her. They were pretending to be a couple in 'A Flight to Remember' from season 1 and Fry tried to get on dates with Leela ever since. She just didn't show signs of the feelings maybe being mutual before some of the later episodes.
Andreas[DK]