His time has come to play on the Champions Tour, and his challenge now is finding the confidence and consistency he needs to stay competitive in the new environment.
Calcavecchia won 13 tournaments in 30 years on the PGA Tour. Just last month, a strong second round at the British Open put him in second place entering the weekend.
But his last win came in March 2007 at the PODS Championship in Florida. In 23 events last year, he had just three top-10 finishes. This year, he made only eight of 15 cuts. His average finish when qualifying for weekend play is 55.6.
"After I won in 2007 and had a good year when I was 47 years old, I think I just kind of took the next two years off mentally and just kind of checked out and waited until I turned 50," Calcavecchia said. "Even though I thought I was trying and that I could ... play well out there, I just sort of didn't and I lost interest."
Calcavecchia is preparing this week for the 3M Championship, his fifth tournament on the 50-and-over tour.
"The first two were about as opposite as you can get from the last two I played," he said Wednesday.
Calcavecchia, who turned 50 on June 12, finished sixth at 12-under par in his tour debut at the Dick's Sporting Goods Open in late June. He was 16th with an 11-under at the Montreal Championship in early July.
After shooting his first sub-70 score in 20 rounds since March 14, Calcavecchia found himself in second place at the British Open. But he shot 77 and 80 on the weekend and finished 73rd.
Calcavecchia returned to the Champions Tour to finish 14th at the Senior British Open one week later and tied for 24th at last week's U.S. Senior Open.
He was a combined 12-over par at the two major tournaments.
"Overall, after four tournaments I'd give myself a C-plus. I'm playing OK, probably slightly above-average, but certainly nothing great. I haven't had a chance to win yet," Calcavecchia said. "It's tough. These guys are still great players out here."
"I've said for three years that I've been looking forward to getting out here," he said. "The golf is still super-duper competitive, yet it is a little more relaxed. It's not like just because you turn 50 all of sudden you're not any good anymore."
The mental part of the game has made him a streakier player than most, if not all, of his competitors.
"When you've got a strong faith in your swing and what you're doing, three or four bad shots won't affect you that much," he said. "In my case, if I play three or four bad holes in a row, hit a couple of bad iron shots, drive in the junk, then all of the sudden I'm like, 'Jesus, I suck. What am I doing out here?'"
His phone lesson with Peter Kostis before last week's U.S. Senior Open allowed Calcavecchia to hit the ball "better than I scored." He also liked how he hit the ball during a "quick 18" on Tuesday.
So will it be enough to defeat Langer? The defending 3M champion is the hottest player on tour with wins the past two weeks.
"He's the guy to beat for sure," Calcavecchia said. "I played with him the first two days last week, and he didn't do anything spectacular. ... It's not like he's hitting every shot perfect or anything. He's just playing really smart, solid golf, and he hit a lot of putts. He made three or four bombs, and every 6- or 7-footer he needed for par he made."
Coming off a tough travel schedule for the players, including an eight-time-zone change between the Senior British Open in Scotland and last week's U.S. Senior Open outside Seattle, a few of the top names are sitting out this week: Couples, Watson and Corey Pavin.
Tom Lehman, a native of Alexandria, Minn., was scheduled to make his first appearance in the tournament. However, he withdrew on Monday with a right knee injury.
Thanks to strong sponsorships, admission to the tournament is free for the second straight year.
"I want everybody in Minnesota to come out and be part of the event," said tournament director Hollis Cavner. "We want people to come see what we have and enjoy some great golf."