| YTD Earnings = $1,378,094 |
| 2009 Date | Tournament | Jeff's Finish | Par | Scores | Earnings | Money List Rank | Charles Schwab Cup Rank |
| Jan. 23-25 | Mitsubishi Electric Championship at Hualalai
Ka'upulehu-Kona, HI | T4 | 72 | 65-67-70 | $104,750 | T4 | T4 |
| Feb. 13-15 | Allianz Championship
Boca Raton, FL | T36 | 72 | 70-71-71 | $8,861 | 9 | T8 |
| Feb. 20-22 | The ACE Group Classic
Naples, FL | T11 | 72 | 75-69-70 | $35,200 | 9 | T11 |
| Mar. 6-8 | Toshiba Classic
Newport Beach, CA | T9 | 71 | 69-68-69 | $44,200 | 7 | 10 |
| Mar. 13-15 | AT&T Champions Classic
Valencia, CA | 10 | 72 | 69-70-71 | $41,600 | 11 | 11 |
| Mar. 27-29 | The Cap Cana Championship
Cap Cana, Dominican Republic | T64 | 72 | 74-73-75 | $2,625 | 14 | 15 |
| Apr. 17-19 | Outback Steakhouse Pro-Am
Tampa, FL | T21 | 71 | 72-70-71 | $17,995 | 16 | 16 |
| Apr. 24-26 | Liberty Mutual Legends of Golf
Savannah, GA | T2 | 72 | 63-65-61 | $132,500 | 10 | 7 |
| May 15-17 | Regions Charity Classic
Birmingham, AL | T34 | 72 | 71-70 | $9,282 | 11 | 9 |
| May 21-24 | Senior PGA Championship*
Beachwood, OH | T5 | 70 | 70-68-70-73 | $65,500 | 9 | 8 |
| May 29-31 | The Principal Charity Classic
West Des Moines, IA | T12 | 71 | 68-71-69 | $35,075 | 11 | 9 |
| June 5-7 | Triton Financial Classic
Austin, TX | T24 | 72 | 68-69-79 | $15,640 | 12 | 11 |
| June 26-28 | Dick's Sporting Goods Open
Endicott, NY | T22 | 71 | 68-67-72 | $18,645 | 14 | 13 |
| July 10-12 | 3M Championship
Blaine, MN | T16 | 72 | 72-70-67 | $27,169 | 13 | 14 |
| July 23-26 | The Senior Open Championship*
Berkshire, England | 24 | 70 | 69-70-69-70 | $20,400 | 14 | 15 |
| July 30-Aug. 2 | U.S. Senior Open Championship*
Carmel, IN | T16 | 72 | 69-74-71-70 | $42,871 | 14 | 15 |
| Aug. 20-23 | JELD-WEN Tradition*
Sunriver, OR | T11 | 72 | 71-72-69-68 | $52,050 | 15 | 21 |
| Aug. 28-30 | Boeing Classic
Snoqualmie, WA | T9 | 72 | 72-69-68 | $48,600 | 15 | 19 |
| Sept. 4-6 | Wal-Mart First Tee Open at Pebble Beach
Pebble Beach, CA | 1 | 72 | 65-73-68 | $315,000 | 5 | 9 |
| Sept. 18-20 | Greater Hickory Classic at Rock Barn
Conover, NC | T6 | 72 | 67-69-67 | $63,000 | 5 | 9 |
| Sept. 25-27 | SAS Championship
Cary, NC | T50 | 72 | 71-72-72 | $6,090 | 5 | 9 |
| Oct. 1-4 | Constellation Energy Senior Players Championship*
Timonium, MD | T24 | 70 | 74-68-66-72 | $24,685 | 6 | 13 |
| Oct. 16-18 | Administaff Small Business Classic
The Woodlands, TX | T30 | 72 | 73-73-70 | $11,754 | 8 | 13 |
| Oct. 23-25 | AT&T Championship
San Antonio, TX | T10 | 71 | 69-67-72 | $39,100 | 8 | 13 |
| Oct. 29-Nov. 1 | Charles Schwab Cup Championship
Sonoma, CA | T3 | 72 | 66-69-70-68 | $195,500 | 6 | 7 |
