SE Asia sounds like it good be a good option, then. They're nuts on football in most of SE Asia, and you will be able to see English premiership, Italian, Spanish, etc. football most places... Oh, I love making suggestions for other folks!! :)
OK, so using trains, how about doing something like:
Fly into Singapore, and work your way up through Malaysia, to Bangkok (one train line - get on and off where you think will be interesting. i.e. KL, Penang, Georgetown, Cameron Highlands, some of the Southern Thai islands for beaches and chilling. Depends on interests and time schedule.)
Spend a few days round and about Bangkok - see some Muay Thai boxing, visit Kanchanaburi for Bridge over the River Kwai, and info on the 'Death Railway' to/from Burma, WWII graveyards, etc.
Then sleeper train from BKK to Chiang Mai in northern Thailand - this is a pretty good experience, and train is clean and comfortable.
Fly from Chiang Mai to Siem Reap. See Angkor Wat, etc for a few days. Explore a bit of Cambodia down to Phnom Penh if you fancy that - I love Cambodia, and would happily spend lots of time there, but depends on your time schedule, etc.
Fly to Hanoi, and then work your way down Vietnam on the Reunification Express train. We did this mainly by sleeper train, which is fairly basic, but a good way to see the country. You'd have a 4 berth cabin to yourselves, and they lock, so quite safe. Just take your own silk/cotton sleeping 'liners' for the bunks (you can buy them in the markets really cheaply).
We stopped in Hue, Hoi An (well, Da Nang, and bussed to Hoi An), Nha Trang and finished in Ho Chi Minh City.
Fly back to BKK or Singapore for your flight home.
Reckon that's do-able in 2-3 months?? I've done this trip, but in bits - and with more added on, so if you were interested in any of it, please PM me, and I can give you travel notes if there was anything there you thought might help with your thinking.