what player has had the most wins as an underdog ever in playoffs

Tiger Woods has the most career tournament wins, with 82 tournament wins.

NAME WINS EVENTS TOP 10 ROUNDS MONEY
1 Tiger Woods
T. Woods
82
1031
198
1,392
$120,999,166
2 Phil Mickelson
P. Mickelson
45
1779
198
2,273
$94,798,661
3 Vijay Singh
V. Singh
34
1892
185
2,224
$71,281,216
4 Rory McIlroy
R. McIlroy
28
324
129
956
$100,633,170
5 Dustin Johnson
D. Johnson
24
587
113
1,052
$73,979,212
6 Davis Love III
D. Love III
21
2418
180
2,739
$44,959,243
7 Tom Watson
T. Watson
21
1094
130
1,406
$9,414,928
8 Greg Norman
G. Norman
20
835
129
1,229
$14,012,818
9 Ernie Els
E. Els
19
1257
126
1,611
$49,385,598
10 Nick Price
N. Price
18
1580
137
1,739
$20,576,105
11 Jim Furyk
J. Furyk
17
1827
188
2,250
$71,507,269
12 Tom Kite
T. Kite
17
1698
156
1,878
$10,251,882
13 Justin Thomas
J. Thomas
16
240
87
896
$68,215,791
14 Mark O'Meara
M. O'Meara
16
2132
119
2,282
$14,325,370
15 Curtis Strange
C. Strange
16
1608
115
1,829
$7,400,933
16 Corey Pavin
C. Pavin
15
2172
108
2,269
$16,021,370
17 Fred Couples
F. Couples
15
2087
162
2,330
$22,860,333
18 Scottie Scheffler
S. Scheffler
14
128
65
484
$78,339,833
19 Adam Scott
A. Scott
14
829
114
1,442
$68,056,617
20 Kenny Perry
K. Perry
14
2073
104
2,216
$32,123,129
21 Hal Sutton
H. Sutton
14
2057
124
2,154
$15,267,686
22 Lanny Wadkins
L. Wadkins
14
1519
89
1,607
$5,422,820
23 Jordan Spieth
J. Spieth
13
283
92
1,009
$64,721,457
24 Jason Day
J. Day
13
604
98
1,201
$63,333,727
25 David Duval
D. Duval
13
1003
68
1,264
$18,983,931
StatMuse has season-level data for tournament wins going back to the 1980 season.