I'll be travelling solo in early May - Madrid for 5 days (maybe a side trip to a city to be determined), Granada for one.
I'll be staying in the touristy area of both Granada and Madrid. What I'm looking for are a tapas bar in Granada, 1 high end restaurant ($100-150 without wine) in Madid where I won't feel awkward dining solo, and suckling pig (this is where a side trip could come in - seems like Segovia may be the place to go), I can fill in the rest of my meals by combing the board.
Also, are there sports bars or the equivalent? I'll be in Madrid the day of the Madrid Barcelona match up and would be interested in watching the game somewhere.
Basically every bar in Granada will serve free tapas with each drink and the tapas get better with each drink. The first one may be some machego cheese, while the next may be some chorizo, then potatoes or anchovies, etc. In Madrid I really liked Olsen for a high end dinner, perhaps bit awkward for dining alone, but really good food. I would recommend Camarilla on Calle Cava Baja in La Latina area right off the Plaza Mayor. Eat at the bar and the bar staff are very friendly and accommodating.
In Madrid, almost every tapas places will have a television on. Also pubs in central Madrid, especially around Sol will have will televise that match. High end restaurants: La Broch for experimental Spanish; less experimental but still modern are Arce, Sacha; Viridiana for more eclectic. I've dined solo in all of the above and do not feel awkward but that is a personal thing. A great seafood place: El Combarro
For Granada, you will find some good tapa places around Plaza Bib-Rambla, Plaza Carmen, especially on c/Navas and around Plaza Nueva.