Comparing Randy and Monson is kind of like comparing apples and oranges, they have two totally different fighting styles.
When monson shoots for a takedown he goes for a double or single leg, randy tends to try to go for a throw or a trip with underhooks from the clinch. Randy has better standup than monson as well, though at his age he would be a fool to try to exchange with sylvia on the feet.
Monson is a submission wrestler, while randy is a classic ground and pound against the fence guy.
Randy's best bet to win the fight is dirty boxing in the clinch, and takedowns with underhooks. I can't remember ever seeing Sylvia fighting in the clinch that much and it might be a soft spot for randy to exploit. Though I'm sure militech is working on that with TIm.
The real problem that randy faces is getting past Tim's reach and into the clinch. Over and over again he has been caought rushing in to the clinch with his arms out, chin out, just waiting for a bomb to drop. Sometimes the other guy misses (belfort scraping his eye) , sometimes he get's hit and shakes it off (van arsedale, over and over again), and sometimes he get's dropped (chuck).
If randy can successfully get into the clinch with Big Tim, not get popped on the way in, and jockey into position for a takedown at least once each round, he stands a chance of a decision win. It's an extremely slim chance, but it's really the only option he's got.