Problem: Sentence1: Enter a race.
Sentence2: Enter a drug treatment program.
Q: Does the term enter mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: He doesn't care about how / whether she comes.
Sentence2: I really care about my work.
Q: Does the term care mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: Pay attention.
Sentence2: He paid me 5000 pounds for the car.
Q: Does the term pay mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: This sweater is an all-wool number.
Sentence2: It was one of the best numbers he ever did.
Q: Does the term number mean the same thing in both these sentences?

Answer:
different meanings