Shortly after graduating from Duke University in 1981, Bolling attempted to earn membership on the PGA Tour.

[1] His parents belonged to a country club which, Bolling later stated, helped him easily segue into golf.

In the first round he shot a 73, leading Duke to a 297 total, six in front of the favored team of Wake Forest University.

[7] Later in the academic year, in April 1979, Bolling played well at the ACC Championship in Greensboro, North Carolina.

At the end of the first round, Bolling was tied for third place with a 69, three back of leader Robert Wrenn of Wake Forest.

As a team, "surprising" Duke was in second place at 371, six back of University of North Carolina at Chapel Hill.

[6] To resolve the problems Bolling moved to Fort Lauderdale, Florida and worked with swing instructor Lew Worsham.

However, von Tacky played excellently on the final round's front nine and after a 25-foot birdie putt on the 8th hole he took the solo lead.

Bolling played the hole poorly but von Tacky "missed a nine-footer for par that would have tied."

He shot an even-par first round 72 to tie several players for the lead, including Mike Cook from the University of Georgia.

[10] In March 1981, it was noted by Raleigh, North Carolina's The News and Observer that Bolling had "rapidly blossomed" over the course of the academic year.

[14] Later in the academic year, at golf's NCAA championships held in Palo Alto, California, Bolling finished in 8th place.

[21] However, Bolling played poorly in the final round, shooting a 75 (+4), to finish in a tie for eighth, four back of champion Jim Dent.

Bolling started the final round tied with England's Peter Oosterhuis, one back of the joint lead shared by Chi-Chi Rodríguez, Dave Stockton, and Ron Commans.

"[28] Though he had some troubles in the middle of the back nine, he drove the 280-yard par-4 16th hole to create an easy birdie and secure the win.

Bolling later stated, "I wanted to play respectable to show people my win in Everett was not a fluke.

[25] In early March he went on a streak, making the cut in four consecutive events, including a T-12 at the USF&G Classic.

[25][17] In 1987, Bolling opened the year with a top ten finish at the Bob Hope Chrysler Classic.

[25] In his last 12 events he made the cut in seven but only recorded one top-25, a T-14 at the Greater Milwaukee Open, and failed to move into the top 125 of the money list.

Bolling played the 1988 PGA Tour Qualifying School at The Woodlands Country Club in the suburbs of Houston, Texas.

In October he played the Pro-Pro Scramble, a Philadelphia Section PGA event, with Brett Upper, the head pro at Bent Creek.

[56] In September, he played the three-round Philadelphia PGA Section Championship at Conestoga Country Club in Lancaster, Pennsylvania.

[59] In September, he played the three-round Izod Club/Cadillac Met PGA Championship at Quaker Ridge Golf Club in Scarsdale, New York.

[62] The top 25 players earned rights to play the 1997 PGA Championship which was going to be held in the state of New York.

Bolling would play Fresh Meadows from dawn to dusk and members would pay for every par and every birdie he made.

[68] In the second round Bolling shot a 74 (+3) to fall into a tie for second with Mark Brown, one behind leader Rick Hartmann.

In September, he recorded a joint runner-up at the Key Food Met PGA Senior Championship.

He won the Polo Golf Met PGA Head Professional Championship and the Senior Treiber Memorial Tournament of Champions for the fourth time.

[75] In 2016 he won the Met PGA Team Championship, a pairs event, with teammate Bill Van Orman.

[75] The following week he successfully defended his Polo Golf Met PGA Head Professional Championship.