| YTD Earnings = $540,305 |
| 2008 Date | Tournament | Jeff's Finish | Par | Scores | Earnings | Money List Rank | Charles Schwab Cup Rank |
| Jan. 18-20 | MasterCard Championship at Hualalai
Ka'upulehu-Kona, HI | | | Did Not Play | | n/a | |
| Jan. 25-27 | Turtle Bay Championship
Kahuku, HI | T23 | 72 | 72-74-73 | $16,400 | n/a | |
| Feb. 8-10 | Allianz Championship
Boca Raton, FL | T18 | 71 | 72-67-71 | $20,171 | 43 | |
| Feb. 15-17 | The ACE Group Classic
Naples, FL | T6 | 72 | 68-68-68 | $60,800 | 21 | |
| Feb. 23-24 | Wendy's Champions Skins Game
| | | Did Not Play | | | |
| Mar. 7-9 | Toshiba Classic
Newport Beach, CA | T13 | 71 | 68-65-72 | $28,114 | 24 | 28 |
| Mar. 14-16 | AT&T Champions Classic
Valencia, CA | T30 | 72 | 70-70-78 | $11,800 | 23 | 28 |
| Mar. 28-30 | Ginn Championship at Hammock Beach Resort
Palm Coast, FL | | | Did Not Play | | | |
| Apr. 4-6 | The Cap Cana Championship
Cap Cana, Dominican Republic | T25 | 72 | 74-71-69 | $18,240 | 34 | 40 |
| Apr. 18-20 | Outback Steakhouse Pro-Am
Lutz, FL | T8 | 71 | 70-71-68 | $46,750 | 29 | 29 |
| Apr. 25-27 | Liberty Mutual Legends of Golf
Savannah, GA | 2 | 72 | 62-63-61 | $132,000 | 17 | 16 |
| May 2-4 | FedEx Kinko's Classic
Austin, TX | T13 | 72 | 68-73-71 | $28,800 | 18 | 16 |
| May 16-18 | Regions Charity Classic
Birmingham, AL | 3 | 72 | 69-72-64 | $122,400 | 13 | 15 |
| May 22-25 | Senior PGA Championship*
Rochester, NY | T9 | 70 | 70-73-70-78 | $50,000 | 11 | 8 |
| May 30-June 1 | The Principal Charity Classic
West Des Moines, IA | T50 | 71 | 70-71-74 | $4,830 | 13 | 10 |
| June 20-22 | Bank of America Championship
Concord, MA | | 73 | | | | |
| June 27-29 | Commerce Bank Championship
East Meadow, NY | | 71 | | | | |
| July 4-6 | Dick's Sporting Goods Open
Endicott, NY | | 72 | | | | |
| July 18-20 | 3M Championship
Blaine, MN | | 72 | | | | |
| July 24-27 | The Senior Open Championship*
Ayrshire, Scotland | | 71 | | | | |
| July 31-Aug. 3 | U.S. Senior Open Championship*
Colorado Springs, CO | | 72 | | | | |
| Aug. 14-17 | JELD-WEN Tradition*
Sunriver, OR | | 72 | | | | |
| Aug. 22-24 | Boeing Classic
Snoqualmie, WA | | 72 | | | | |
| Aug. 29-31 | Wal-Mart First Tee Open at Pebble Beach
Monterey, CA | | 72 | | | | |
| Sept. 12-14 | Greater Hickory Classic at Rock Barn
Conover, NC | | 72 | | | | |
| Sept. 26-28 | SAS Championship
Cary, NC | | 72 | | | | |
| Oct. 9-12 | Constellation Energy Senior Players Championship
Timonium, MD | | 70 | | | | |
| Oct. 17-19 | Administaff Small Business Classic
Spring, TX | | 72 | | | | |
| Oct. 24-26 | AT&T Championship
San Antonio, TX | | 71 | | | | |
| Oct. 30-Nov. 2 | Charles Schwab Cup Championship
Sonoma, CA | | 72 | | | | |