The 1999 WGC-American Express Championship was a golf tournament that was contested from 4–7 November 1999 at Valderrama Golf Club in Sotogrande, San Roque, Spain. It was the first WGC-American Express Championship tournament, and the third and final event in the inaugural year of the World Golf Championships.

World number 1, Tiger Woods won the tournament after defeating Miguel Ángel Jiménez in the first extra hole of a playoff. Woods held a four stroke lead going into the 17th hole but hit it into the water on the tough par 5 and ended up scoring a triple bogey that allowed Jiménez to get back in it.

1. Top 50 from the Official World Golf Ranking as of 1 November

Stuart Appleby (2), Stewart Cink, Darren Clarke (3), Glen Day, Steve Elkington, Ernie Els (2,3), Bob Estes (2), Carlos Franco (2), Fred Funk (2), Jim Furyk (2), Sergio García (3), Brent Geiberger (2), Retief Goosen (3), Pádraig Harrington (3), Dudley Hart, Tim Herron (2), Scott Hoch, John Huston (2), Miguel Ángel Jiménez (3), Bernhard Langer (3), Paul Lawrie (3), Tom Lehman (2), Justin Leonard (2), Davis Love III (2), Jeff Maggert (2), Phil Mickelson (2), Colin Montgomerie (3), José María Olazábal, Naomichi Ozaki (6), Craig Parry, Steve Pate (2), Chris Perry (2), Nick Price (2), Loren Roberts (2), Vijay Singh (2), Jeff Sluman (2), Hal Sutton (2), David Toms (2), Bob Tway, Brian Watts, Lee Westwood (3), Tiger Woods (2)

• Payne Stewart (2) died in a plane crash on 25 October.
• Fred Couples, David Duval (2), Lee Janzen, Mark O'Meara, Masashi Ozaki, Jesper Parnevik, and Steve Stricker did not play.

2. Top 30 on the 1999 PGA Tour money list through the Tour Championship

Notah Begay III, Dennis Paulson, Ted Tryba, Duffy Waldorf, Mike Weir

3. Top 20 on the 1999 European Tour Order of Merit through the Volvo Masters

Thomas Bjørn, Ángel Cabrera, Alex Čejka, Mark James, Robert Karlsson, Bob May, Jarrod Moseley (4), Jarmo Sandelin, Jean van de Velde

• John Bickerton did not play.

4. Top 3 on the 1998–99 PGA Tour of Australasia Order of Merit

Rod Pampling, Craig Spence

5. Top 3 on the 1998–99 Southern Africa Tour Order of Merit

Scott Dunlap, David Frost, Richard Kaplan

6. Top 3 on the 1999 Japan Golf Tour Order of Merit through the Philip Morris Championship

Kazuhiko Hosokawa

• Shigeki Maruyama did not play.

Place	Player	Score	To par
1	Vijay Singh	67	−4
2	Jim Furyk	68	−3
T3	Bob Estes	69	−2
	Scott Hoch
	Mark James
	Phil Mickelson
	Nick Price
T8	Jeff Maggert	70	−1
	Colin Montgomerie
	Chris Perry
	Jarmo Sandelin

Place	Player	Score	To par
T1	Tim Herron	71-66=137	−5
	Chris Perry	70-67=137
T3	Justin Leonard	71-67=138	−4
	Vijay Singh	67-71=138
T5	Fred Funk	71-68=139	−3
	Scott Hoch	69-70=139
	Mark James	69-70=139
	Tom Lehman	72-67=139
T9	Stewart Cink	75-65=140	−2
	Miguel Ángel Jiménez	72-68=140
	Phil Mickelson	69-71=140
	Nick Price	69-71=140
	David Toms	72-68=140
	Lee Westwood	73-67=140
	Tiger Woods	71-69=140

Place	Player	Score	To par
T1	Miguel Ángel Jiménez	72-68-69=209	−4
	Chris Perry	70-67-72=209
T3	Tom Lehman	72-67-71=210	−3
	Justin Leonard	71-67-72=210
	Nick Price	69-71-70=210
	Hal Sutton	75-66-69=210
	Tiger Woods	71-69-70=210
T8	Stewart Cink	75-65-71=211	−2
	Scott Hoch	69-70-72=211
	José María Olazábal	73-69-69=211
	David Toms	72-68-71=211
	Lee Westwood	73-67-71=211

Place	Player	Score	To par	Money ($)
T1	Tiger Woods	71-69-70-68=278	−6	Playoff
	Miguel Ángel Jiménez	72-68-69-69=278
3	Dudley Hart	75-68-70-70=283	−1	300,000
T4	Stewart Cink	75-65-71-73=284	E	176,667
	Nick Price	69-71-70-74=284
	Lee Westwood	73-67-71-73=284
T7	Fred Funk	71-68-74-72=285	+1	135,000
	Sergio García	74-69-69-73=285
	Scott Hoch	69-70-72-74=285
	Chris Perry	70-67-72-76=285

Place	Player	Score	To par	Money ($)
1	Tiger Woods	3	−1	1,000,000
2	Miguel Ángel Jiménez	5	+1	400,000

• Played on the par-4 18th hole,

• Full results

36°17′09″N 5°20′02″W / 36.28583°N 5.33389°W / 36.28583; -5.33389