Between the 2014-15 and 2019-20 seasons, Dustin Johnson had the most tournament wins, with 15 tournament wins.

most pga tour wins 2014-15 to 2019-20
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JohnsonThomasSpiethDayMcIlroyKoepkaDeChambeauWatsonReedRahmSchauffeleMatsuyamaFowlerLeishmanRoseMorikawaWalkerHermanSnedekerScottNaKisner15131010876655444443333333
NAMEEVENTSWINSTOP 10ROUNDSMONEY
Dustin JohnsonDustin Johnson1151559426$43,138,583
Justin ThomasJustin Thomas1441353510$37,378,435
Jordan SpiethJordan Spieth1311047468$32,891,242
Jason DayJason Day1171042395$30,095,462
Rory McIlroyRory McIlroy95848338$28,158,076
Brooks KoepkaBrooks Koepka119739412$30,407,970
Bryson DeChambeauBryson DeChambeau95625321$18,096,270
Bubba WatsonBubba Watson123630412$20,509,853
Patrick ReedPatrick Reed155539564$25,175,423
Jon RahmJon Rahm78537290$21,065,855
Xander SchauffeleXander Schauffele94424334$17,783,304
Hideki MatsuyamaHideki Matsuyama135440485$26,021,582
Rickie FowlerRickie Fowler119439434$23,698,546
Marc LeishmanMarc Leishman137429470$19,963,032
Justin RoseJustin Rose104441368$25,248,533
Collin MorikawaCollin Morikawa30310113$7,005,758
Jimmy WalkerJimmy Walker130316433$12,492,777
Jim HermanJim Herman13238390$6,625,106
Brandt SnedekerBrandt Snedeker136330471$15,586,060
Adam ScottAdam Scott99328360$17,881,715
Kevin NaKevin Na145331488$16,620,435
Kevin KisnerKevin Kisner156333540$20,487,410
Webb SimpsonWebb Simpson131336470$21,870,992
Tiger WoodsTiger Woods48313177$11,175,092
Daniel BergerDaniel Berger143327483$17,510,349
StatMuse has season-level data for tournament wins going back to the 1979-80 season.