9 1/2 days Madrid - Granada itinerary

I think plan 1 is the best, given your constraints

Dec 1 - arrive, train to Cordoba, leisurely evening wander the town and recover from jet lag
Dec 2 - see the Mesquita in the AM, take a later afternoon bus or train to Granada (ALSA bus may have the most times available, is comfortable and takes about the same time as the train). Arrive in Granada in time for dinner. S
Dec 3 - Dec 4 - Granada. Book the Alhambra well ahead for one of these days.
Dec 5 - to Madrid to get your father, stay in Madrid or Toledo for the rest of your time

I don't love Plan 3 because that gives you extra time in Madrid - you will need to be in Madrid from the 5th on so no need to add extra time when there are other things you are interested in.
Plan 2 is fine, but Cordoba is great and Plan 1 lets you squeeze it in.

No offense, but I can read your mental turmoil. Lots of information but not sure all is relevant.

Essentially, you want to go to Granada and possibly Cordoba between Dec 1 and 5 and want some scheduling help. Is that it?
I always worry about international travel in Canada's 'winter'. Weather, you know. So I hesitate to recommend traveling further on arrival day....unless you are prepared to buy a ticket at the station for whatever train you can catch to Cordoba; or pay for a fully refundable ticket online hoping you can catch the train you want. The good news is that there are trains of some sort or another every 25-35 minutes until midnight from Atocha station.
So, let's consider heading on to Cordoba Friday Dec 1. see what you can see, Dec 2 continue in Cordoba and depart for Granada (most likely bus would be fine) in the late afternoon or when you are 'done', and overnight Granada. Dec 3-4 full days in Granada and then fly to Madrid afternoon of Dec 5th. There is an Iberia flight at 13:30 that isn't too crazy of a price. It means that you arrive where you need to be to pick up dad. It is just an hour, so if Dad is coming in late, then take the train from Granada as flights later in the day are then by Vueling and crazy prices.
For 10 days, you should be able to just pack one carry on size bag so no need to separate luggage but otherwise, look at the luggage check at Atocha station.
Giving yourself permission to stay in Cordoba until Saturday late afternoon or evening may help to reduce the 'stretched thin' feeling; and using the bus means not having to prebook a set time. It gives you time in a city that is negatively impacted with day trippers and allows a little extra jet lag adjustment time.
2 and a half days in Granada is often enough, however, if you wanted to consider a night visit as well as a day visit to Alhambra, then you have to alter plans, as in December, night visits are only Friday and Saturday nights and I expect you will feel rushed trying to arrive Saturday afternoon and making it to the night show at 8 pm to 9:30.
Otherwise, consider going right to Granada and do an overnight stopover in Cordoba on the way back to Madrid arriving in Madrid to meet Dad. This will require a committed train ticket as you may need to leave when every other traveler is trying to leave Cordoba as well.

Thank you kindly, Mira and Maria. Very valuable information and it really helped me root out the option of staying in Madrid the first night.

@Maria (and others who feel the same), no offense taken and I realized that my post is less than ideally organized. I am 'English as a Second Language" speaker which often contributes in how I lay out my thoughts. Also, I wrote about the game (which you might have referred to, at least partially, when you said 'not all is relevant') only in hope that some readers might love the sport and could advise me on which game to go for :)

Well, in certain forums 'the game' would take priority :-)
I hope you can work with what we suggest.

I'll weigh in on the game aspect... Not sure who RM is playing on those days, if it's Barca, it will difficult to procure a ticket. For Champions League, it looks like it will be Dortmund. Although it is still very early in the Champions League tournament, I would suggest this game for the international soccer experience. We have been lucky enough to see World Cup, Euro Cup, Champions League and La Liga games and you are in for a treat whatever you choose. We've had good luck with secondary market site viagogo for tickets, albeit at a premium price. Good luck, have fun, and embrace the exuberance you will be part of no matter what game you choose.

Thank you, Kathleen. Indeed, it is the game against Dortmund and I too am thinking that the international factor of that game will add to the atmosphere. On the other hand, since RM has already secured the spot to the next round of the CL, I wasn't sure if it will draw enough attention. In La Liga however, they had a bad start of the season and Seville is doing pretty well so it will be a fight for each point. El Clasico is only 2 weeks after the game with Seville so local people might calculate carefully which one of these 3 games to see since they're so close. Considering that I absolutely must see a game (that's the present to Dad for his birthday), I might go with VIP tickets for Dortmund game and then see if i can get just the regular tickets for Seville and see both games. I'm very excited - it's going to be many 'dream come true' for me (Prado, Guernica, Alhambra, La Mezquita, a big football game with my dad after so many years...). I travel quite a bit but haven't been this excited about a trip in a long while.
Thanks so much for everyone's help!