Hey Dan, I know for sure you cant parlay Tennis at Olympic. As far as Pinnacle goes, I dont know. Im pretty sure you cant parlay more than 1 sport together there. 5 Dimes is by far the best Americanized Sportsbook for Tennis. Give them a look if you plan on posting up somewhere. They are also very good for all other sports and there are really no guidelines.
Ive been playing there for 6 years and I love it.