OVERVIEW: The Charles Schwab Cup Playoffs began in 2016. It is a three-tournament, season-ending competition to determine the Charles Schwab Cup Champion.
The first Playoffs event in 2019 will be the Dominion Energy Charity Classic (Oct. 12-18) at Richmond’s Country Club of Virginia James River Course. Next up is the Boca Raton Championship (Oct. 26-Nov. 1) at The Old Course at Broken Sound in Boca Raton, Florida. The finale is the the Charles Schwab Cup Championship (Nov. 2-8), the traditional season-ending event which will be held at Phoenix Country Club.
Starting in 2018, there will be no points reset entering the Charles Schwab Cup Championship. Instead, double points will be awarded to the 36 players in the finale.
The Charles Schwab Cup winner will earn a $1 million bonus and the top five finishers will also receive bonus payouts.
POINTS SYSTEM: A points system will commence starting with the Dominion Energy Charity Classic. Each player’s current money total before the start of the Playoffs will become the equivalent number of points ($330,000 equals 330,000 points). Double points will be earned by each player competing in all three Playoffs events, including the Charles Schwab Cup Championship.
CHARLES SCHWAB CUP WINNERS
| Year | Winner | Won at Event No. | Clinched | Runner-up |
| 2001 | Allen Doyle | 37 of 37 | SENIOR TOUR Championship | Bruce Fleisher |
| 2002 | Hale Irwin | 32 of 35 | Turtle Bay Championship | Bob Gilder |
| 2003 | Tom Watson | 31 of 31 | Charles Schwab Cup Championship | Jim Thorpe |
| 2004 | Hale Irwin | 30 of 30 | Charles Schwab Cup Championship | Craig Stadler |
| 2005 | Tom Watson | 28 of 28 | Charles Schwab Cup Championship | Dana Quigley |
| 2006 | Jay Haas | 28 of 28 | Charles Schwab Cup Championship | Loren Roberts |
| 2007 | Loren Roberts | 29 of 29 | Charles Schwab Cup Championship | Jay Haas |
| 2008 | Jay Haas | 29 of 29 | Charles Schwab Cup Championship | Fred Funk |
| 2009 | Loren Roberts | 25 of 25 | Charles Schwab Cup Championship | John Cook |
| 2010 | Bernhard Langer | 26 of 26 | Charles Schwab Cup Championship | Fred Couples |
| 2011 | Tom Lehman | 24 of 24 | Charles Schwab Cup Championship | Mark Calcavecchia |
| 2012 | Tom Lehman | 24 of 24 | Charles Schwab Cup Championship | Bernhard Langer |
| 2013 | Kenny Perry | 26 of 26 | Charles Schwab Cup Championship | Bernhard Lange |
| 2014 | Bernhard Langer | 25 of 26 | AT&T Championship | Colin Montgomerie |
| 2015 | Bernhard Langer | 24 of 24 | Charles Schwab Cup Championship | Colin Montgomerie |
| 2016 | Bernhard Langer | 26 of 26 | Charles Schwab Cup Championship | Colin Montgomerie |
| 2017 | Kevin Sutherland | 26 of 26 | Charles Schwab Cup Championship | Bernhard Langer |
| 2018 | Bernhard Langer | 26 of 26 | Charles Schwab Cup Championship | Scott McCarron |
| 2019 | Scott McCarron | 26 of 26 | Charles Schwab Cup Championship | Jerry Kelly |
PRIZE MONEY ($2.1 million annuity to the top-five point earners at season's end)
| Place | Money |
| 1st | $1 million |
| 2nd | $500,000 |
| 3rd | $300,000 |
| 4th | $200,000 |
| 5th | $100,000 |
