I was counting on getting a raise.

[beachboy]

1 - Carol was counting upon getting a raise in the spring.
2 - I was counting on getting a raise when I made the decision to purchase a penthouse. (Both sentences from The Free Dictionary)

In both of the sentences above, does was counting on necessarily mean that neither Carol nor I got a raise?

[SoothingDave]

Context will tell. Generally, it would be something that did not happen, but it is possible that one could say "I was counting on getting the raise when I bought that new car, and luckily it came through the next month."

[probus]

Notwithstanding the impressive mental gymnastics SoothingDave displayed in constructing his perfectly valid example, when "counting on" is used the context is usually* one of disappointment.

*this originally said "almost invariably one of disappointment". In view of the examples provided by SoothingDave and emsr2d2 I realized that claim was excessive.

[jutfrank]

In sentence 1 we just don't know, since the spring is in the future at the time of utterance. It's about her expectations of getting a raise.

In sentence 2, without further context, I'd say there is an implication that the raise did not happen.

[Tarheel]

Carol was counting on getting a raise in the spring.

She was disappointed when she didn't get one.

[jutfrank]

Carol was counting on getting a raise in the spring.

She was disappointed when she didn't get one.

Possibly, yes, but then it would be more likely as:

Carol had been counting on getting a raise in the spring. She was disappointed when she didn't get one.

[emsr2d2]

I would only associate "counting on" with disappointment if the sentence referred to the past and was clear about the disappointment. Otherwise, it expresses a neutral or even an optimistic positivity.

Me: I've put a £5 bet on you winning your tennis match tomorrow.
Seb: I'll do my best.
Me: I'm counting on you! I'm taking my girlfriend out for dinner with the winnings!

Helen: How did you do at the pub quiz last night?
John: It was nerve-wracking. We were tied for first place at the end of the main rounds.
Helen: What happened?
John: We had to play a tiebreak.
Helen: What did you have to do?
John: One person from each team went up to the front of the pub and then the quizmaster asked one single general knowledge question. The first one to shout out the correct answer would be the winner.
Helen: Who went up for your team?
John: I did! It was terrifying. The team was counting on me to shout the correct answer out first.
Helen: And did you?
John: Yes! We won £100!