Played as the Royal Caribbean Classic (Feb 6-8). Second-placed Dana Quigley (USA) finished 1 shot behind Fleisher (USA). [Crandon Golf at Key Biscayne, nr Miami, FL; at the time known as Crandon Pk GC].

Played as Bruno's Memorial Classic (Apr 30-May 2). Second-placed Bruce Lietzke (USA) and D.A. Weibring (USA) finished 7 shots behind Fleisher (USA), who recorded the last of his 18 Champions Tour wins. [Greystone G&CC, Birmingham, Alabama].

Played as the Verizon Classic (Feb 21-23). Second-placed Hale Irwin (USA) finished 1 shot behind Fleisher (USA). [TPC Tampa Bay, Lutz, nr Tampa, FL].

Played as the RJR Championship (Sept 13-15; not played in 2001). Second-placed Hale Irwin (USA) finished 5 shots behind Fleisher (USA). [Championship course, Tanglewood Golf, Clemmons, nr Winston-Salem, NC].

The US Senior Open (Jun 29-Jul 1). Second-placed Gil Morgan (USA) and Isao Aoki (Jpn) finished 1 shot behind Fleisher (USA). [Salem CC, Peabody, Mass.].

Played as the Home Depot Invitational (May 4-6). Second-placed John Bland (RSA) finished 3 shots behind Fleisher (USA), who won this event for the third straight year. [TPC Piper Glen, Charlotte, North Carolina].

Played as the Las Vegas Senior Classic (April 20-22). Second-placed Larry Nelson (USA), Doug Tewell (USA), Hale Irwin (USA), Walter Hall (USA), José Maria Cañizares (Esp) and Vicente Fernández (Arg) finished 3 shots behind Fleisher (USA). [TPC Summerlin, Las Vegas, Nevada].

Played as the AIB Irish Seniors Open (May 12-14). Second-placed George Burns (USA) and Bob Shearer (Aus) finished 3 shots behind 51-year-old Bruce Fleisher (USA), who recorded his only win on the European Senior Tour. [Tulfarris GC, Blessington, Co. Wicklow].

Played as the Lightpath Long Island Classic (July 28-30). Second-placed Dana Quigley (USA) finished 2 shots behind defending champion Fleisher (USA). [Meadow Brook Club, Jericho, Long Island, NY].

Played as the Home Depot Invitational (May 5-7). Fleisher (USA) beat Hubert Green (USA) with a birdie at the third playoff hole. [TPC Piper Glen, Charlotte, North Carolina].

Played as the Royal Caribbean Classic (Feb 3-6; played on a modified stableford basis). Second-placed Vicente Fernandez (Arg) finished 2 pts behind defending champion Fleisher (USA). [Crandon Golf at Key Biscayne, nr Miami, FL; at the time known as Crandon Pk GC].

Played as the GTE Classic (Feb 18-20). Second-placed Dana Quigley (USA) finished 4 shots behind Fleisher (USA). [TPC Tampa Bay, Lutz, nr Tampa, FL].

Played as the Home Depot Invitational (April 23-25). Second-placed Terry Dill (USA) and Jim Holtgrieve (USA) finished 1 shot behind Fleisher (USA). [TPC Piper Glen, Charlotte, North Carolina].

Played as the BellSouth Senior Classic at Opryland (June 11-13). Second-placed Al Geiberger (USA) finished 1 shot behind Fleisher (USA). [Gaylord Springs Links, Nashville, Tennessee; at the time known as Springhouse GC].

Fleisher (USA) won the Byron Nelson Award, recording the season's lowest scoring average on the Senior PGA Tour. Hale Irwin (USA) was second with 69.58; Gil Morgan (USA) was third with 69.69.

Fleisher (USA) won the Arnold Palmer Award as the Senior PGA Tour 1999 leading money winner, with earnings of $2,515,705 on the Tour. Hale Irwin (USA) was second with $2,025,232; Allen Doyle (USA) was third with $1,911,640.

Fleisher (USA) won the Jack Nicklaus Award as the Senior PGA Tour Player of the Year, based on the votes of his peers..

Played as the Lightpath Long Island Classic (Aug 6-8). Second-placed Allen Doyle (USA) finished 2 shots behind Fleisher (USA). [Meadow Brook Club, Jericho, Long Island, NY].

Fleisher (USA) won the Senior PGA Tour 1999 Rookie of the Year Award as the leading first-season player, based on the votes of his peers. He also finished top of the Tour's money list, with earnings of $2,515,705.

Played as the Royal Caribbean Classic (Feb 5-7). Second-placed Isao Aoki (Jpn) finished 2 shots behind first-time Senior PGA Tour winner Fleisher (USA). [Crandon Golf at Key Biscayne, nr Miami, FL; at the time known as Crandon Pk GC].

Played as The Transamerica (Oct 8-10). Second-placed Allen Doyle (USA) finished 1 shot behind Fleisher (USA). [South course, Silverado Resort, Napa, California].

Played as the American Express Invitational (Feb 12-14). Second-placed and defending champion Larry Nelson (USA) finished 3 shots behind Fleisher (USA), who recorded back-to-back wins on the Senior PGA Tour. [TPC Prestancia, Sarasota, Florida].

Played as the EMC Kaanapali Classic (Oct 22-24). Second-placed Allen Doyle (USA) finished 1 shot behind Fleisher (USA). [Royal Ka'anapali course, Ka'anapali Resort, Maui, Hawaii; at the time known as the North course].

Played as the New England Classic (July 11-14). 42-year-old Bruce Fleisher (USA) beat Ian Baker-Finch (Aus) with a birdie at the seventh playoff hole, to claim his first and only win on the PGA Tour. [Pleasant Valley CC, Sutton, MA].

Played as the Jamaica Open (Nov 15-18). Won by Fleisher (USA). [Half Moon Resort, Rose Hall, nr Montego Bay, Jamaica].

Played as the Panama Open. Won by Fleisher (USA).

Played as the Brazil Open (Aberto do Brasil). Fleisher (USA) beat 17-year-old Jaime Gonzalez Jnr (Brazil, amateur) with a birdie at the third playoff hole. [Itanhangá GC, Itanhangá, Rio de Janeiro].

The US Amateur Championship (68th) (Aug 28-31). Second-placed Marvin "Vinny" Giles III (USA) finished 1 shot behind Bruce Fleisher (USA). [Scioto CC, Columbus, Ohio].