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Between the 1998 and 1999 seasons, Tiger Woods had the most tournament wins, with 9 tournament wins.

most wins by a golfer in 1998 to 1999
WoodsDuvalSinghSuttonBegayElsApplebyMickelsonTomsWaldorfBrowneFurykCouplesFrancoSlumanParnevikHustonMayfairElkingtonO'MearaStewartBeem9833222222222222222221
NAMEWINSEVENTSTOP 10ROUNDSMONEY
Tiger WoodsTiger Woods916029152$8,457,702
David DuvalDavid Duval816524157$6,232,937
Vijay SinghVijay Singh320418194$4,522,231
Hal SuttonHal Sutton319522194$3,966,318
Notah BegayNotah Begay2101297$1,255,314
Ernie ElsErnie Els211611108$2,474,539
Stuart ApplebyStuart Appleby216410155$2,077,686
Phil MickelsonPhil Mickelson216815157$3,559,927
David TomsDavid Toms219610196$2,594,745
Duffy WaldorfDuffy Waldorf21765172$1,592,876
Olin BrowneOlin Browne21655157$1,424,571
Jim FurykJim Furyk220120197$3,881,927
Fred CouplesFred Couples212711124$2,419,581
Carlos FrancoCarlos Franco271783$1,885,663
Jeff SlumanJeff Sluman221811225$2,769,866
Jesper ParnevikJesper Parnevik21449135$2,346,290
John HustonJohn Huston217515173$3,063,497
Billy MayfairBilly Mayfair21829173$2,023,418
Steve ElkingtonSteve Elkington2737113$1,782,151
Mark O'MearaMark O'Meara213210131$2,655,495
Payne StewartPayne Stewart214511148$3,271,946
Rich BeemRich Beem168270$610,555
Paul LawriePaul Lawrie10116$562,234
Davis Love IIIDavis Love III116123152$4,016,480
Mark CalcavecchiaMark Calcavecchia119811199$2,102,525
Tim HerronTim Herron
Jose Maria OlazabalJose Maria Olazabal
Mike WeirMike Weir
Lee WestwoodLee Westwood
Steve JonesSteve Jones
Scott SimpsonScott Simpson
Michael BradleyMichael Bradley
Fred FunkFred Funk
Lee JanzenLee Janzen
Glen DayGlen Day
Justin LeonardJustin Leonard
Trevor DoddsTrevor Dodds
Brian HenningerBrian Henninger
Jeff MaggertJeff Maggert
Brad FaxonBrad Faxon
J.P. HayesJ.P. Hayes
Rocco MediateRocco Mediate
Loren RobertsLoren Roberts
Chris PerryChris Perry
Brandel ChambleeBrandel Chamblee
John CookJohn Cook
Ted TrybaTed Tryba
Tom PerniceTom Pernice
Brent GeibergerBrent Geiberger
Gabriel HjertstedtGabriel Hjertstedt
StatMuse has season-level data for tournament wins going back to the 1980 season.

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