A lot of the best matches were never recorded or seen by very many people. I am sure people who hung in some of the top action rooms would have a hard time picking a favorite there were so many.
My two favorites were Mike Carella playing Larry Hubbart in the Congress Billiards in Miami. They played for days only taking brief breaks for a little nap. They played anywhere from 1 to 3 thousand a game 9-ball depending on the side action. During the match the game had 20 and 30 thousand dollar swings with each player showing the heart to come back. In the end Mike won a substantial amount. About that same time maybe a week or two later Mike also played Jim Mataya for several days as well and Mike beat him soundly. I have a feeling if you ask Mataya he will not admit to it but a lot of us were there and saw it.
http://www.josscues.com/photo_gallery/more_greats/image/great-24-carella.jpg
My second favorite was a pay ball game played in Dayton Ohio around 1973 a Joe Burns place. It went on for a week with some of the best players in the world of that time playing. It was one of the best exhibitions of play you could ever have the pleasure of watching. Tens of thousands changed hands as player after player took their shot at the game.
Those were the days when we had so many strong road men traversing the country. Maybe 50-100 very strong players all crisscrossing the highways looking for action. Probably another couple of hundred good players out on the road then as well. There were tons of poolrooms and action to be found everywhere. Even a shortstop like me could make money if he was careful.
I was in Dayton for that tournament and Denny Searcy ended up the big winner, something like 26K! That was big money forty years ago. To this day I've never seen anyone who could play like him on a snooker table. He cut balls down the rail and into those tiny pockets, that most of us couldn't make with ball in hand from two feet away! How he did it I have no idea. Denny was a freak! Denny was the one guy who may have been able to beat Mike Carella at the Congress Bowl back then. He was that good and had zero quit in him.
There were a lot of truly great money players around back in the 70's. Greg Stevens, Hubbart, Sigel, Buddy, Toby Sweet, Richie Florence, Ronnie, Ed Kelly, Billy Johnson aka Wade Crane, Don Watson, Bernie Schwartz, Billy I., Jersey Red, Eddie Taylor, Boston Shorty, Jimmy Moore, Harold Worst, Lassiter, Jimmy Marino, Mataya, Jimmy Reid and many more just under them. I feel fortunate that I saw them all play in their prime. Too bad Efren and Parica didn't come until the 80's. Although I doubt that anyone could have beaten Parica at 9-Ball or Ten Ball. Maybe only Harold Worst (or Buddy?) had the right stuff to handle Parica's best game. Before he had his stroke in the early 90's, Richie was trying to get back in stroke to challenge Parica. He really wanted to play him. That would have been an epic match because Richie was absolutely fearless and could play forever.