The thirtieth annual Winchester 400 motor race (run yearly since 1970) was held under Kendall Late Model Series sanction on September 26, 1999, at the Winchester Speedway, Indiana (USA).
After turning in a stellar performance the previous year, only to have suspension failure end his hopes of an initial "Winchester 400" victory. Brian Ross of Plymouth, Indiana, had everything go his way in the 1999 running of the 200-miler. This was the first running of the historic event under the sanction of the Kendall Late Model Series and was the first win by an Indiana-based driver since Vern Schrock won the fourth annual event in 1973.
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Matt Hagans of Indianapolis, Indiana, started off the weekend by establishing a new track record fort he series of 15.494 seconds (116.167 MPH). At the green, former Series Champion Brian Rievley jumped from his outside pole position starting spot to the lead, with Hagans, Kenny Tweedy, David Stremme, and Jim Crabtree Jr. in pursuit. Starting 18th in the 32-car field, B. Ross charged to sixth by lap 87.
The first round of pit stops occurred on lap 117 after Peter Cozzolino and Dave Jackson made contact, sending Cozzolino bouncing off the inside front-stretch wall. Ray Skillman elected to stay on the racetrack and was scored the leader, while Ross was forced to make two trips down pit lane and was shuffled to the last car on the lead lap. Skillman would stay out in front until stopping for service on lap 154, setting up a battle among Rievley, Hagans, and B. Ross for the race lead. Rievley and Hagans would trade the lead several times before Hagans suffered oil pump problems and retired.
This handed the lead to back to Rievley on lap 317. After a pair of top-five "400" finishes as a part-time All-Pro Series competitor, Rievley appeared headed for his first win when he suddenly slammed into the fourth turn wall on lap 379. Running a close second, B. Ross was able to avoid Rievley and assume the lead. On the restart, B. Ross was able to cruise home a lap ahead of younger brother Scott Ross who was a late-entry in what was originally the back-up car for the eventual winner. Jeff Fultz was third, six laps back of the leader with Chet Blanton fourth. David Ecoff was credited with fifth, 17 laps behind the leader as high-attrition marred the event. B. Ross collected $10,100 for the biggest win of his career.
| Results of the 30th Annual Winchester 400 | ||||||||
|---|---|---|---|---|---|---|---|---|
| Pos | Start | Car # | Driver/Hometown | Sponsor/Make | Laps | Winnings (in US$) |
Status | |
| 1 | 18 | 42 | Brian Ross / Plymouth, IN | R & R Fabrication/Wade Construction/Pizza Bills / Chevrolet | 400 | $10,100 | running | |
| 2 | 17 | 47 | Scott Ross / Plymouth, IN | R & R Fabrication/Wade Construction / Pontiac | 399 | $7,000 | running | |
| 3 | 12 | 30 | Jeff Fultz / Milford, OH | Vogue Cleaners / Chevrolet | 394 | $5,000 | running | |
| 4 | 13 | 5 | Chet Blanton / Plainfield, IN | FOX 59/Hubler Group/Motorsports Spares / Chevrolet | 384 | $3,500 | ||
| 5 | 29 | 15 | David Ecoff / Mohawk, IN | Liquid Transportation Corporation / Chevrolet | 383 | $3,100 | ||
| 6 | 2 | 1 | Brian Rievley / Alexandria, IN | Low Bob’s Cigarettes/Hendricks Parts / Chevrolet | 379 | $2,500 | ||
| 7 | 11 | 45 | Dave Jackson / Loveland, OH | Tri-State Sterling Trucks/Redbank Transport / Chevrolet | 359 | $2,100 | ||
| 8 | 5 | 78 | Bull Baker / Daleville, IN | Stoops Automotive/Ken-Bar Tool & Engineering / Chevrolet | 344 | $1,900 | ||
| 9 | 23 | 28 | Brian Fries / Christianburg, OH | Fries Machine & Tool / Chevrolet | 334 | $1,700 | ||
| 10 | 1 | 9 | Matt Hagans / Indianapolis, IN | Medallion Tortilla Chips/Eagle Creek Aviation/Port City Racing / Chevrolet | 319 | $1,550 | ||
| 11 | 32 | 99 | Eric Nale / Pekin, IN | Stewart Automotive/Zink Signs / Chevrolet | 287 | $1,400 | ||
| 12 | 27 | 14 | Josh Clemons / New Albany, IN | Fuzzy Zoeller’s Barbeque Sauces / Chevrolet | 276 | $1,300 | ||
| 13 | 10 | 67 | Vern Slagh / Zeeland, MI | Riverhaven Village / Chevrolet | 261 | $1,225 | ||
| 14 | 8 | 63 | Jim Crabtree, Jr. / Muncie, IN | Jim’s Automotive Service / Pontiac | 259 | $1,150 | ||
| 15 | 30 | 71 | Al Grogg / Bluffton, IN | Al’s Custom Muffler / Chevrolet | 257 | $1,125 | ||
| 16 | 9 | 73 | Scott Hantz / Pleasant Lake, IN | EMF Corporation / Chevrolet | 251 | $1,100 | ||
| 17 | 14 | 61 | Biff George / Minooka, IL | Pace Pit Equipment/Rod Baker / Ford | 231 | $1,090 | ||
| 18 | 19 | 01 | Joe Williamson / Louisville, KY | SKR Cleaning Services / Chevrolet | 187 | $1,080 | ||
| 19 | 31 | 27 | Ray Skillman / Indianapolis, IN | Dupont Automotive Finishes/Kendall Oil / Ford | 179 | $1,070 | ||
| 20 | 25 | 06 | Royce Mason / Fort Wayne, IN | C & P Machine Shop/Mid-Western Drywall / Chevrolet | 172 | $1,060 | ||
| 21 | 21 | 26 | Rick Turner / Yorktown, IN | Rick’s Service Center/Ultra Racing Engines / Pontiac | 138 | $1,050 | ||
| 22 | 4 | 2 | Kenny Tweedy / Greenfield, IN | EDCO General Contractors/Keith Electric/J & K Auto Color / Ford | 135 | $1,040 | ||
| 23 | 7 | 6 | Peter Cozzolino / Avon, IN | 1st AYD/A & A Manufacturing / Chevrolet | 129 | $1,105 | ||
| 24 | 26 | 79 | Spanks Overbeek / Cincinnati, OH | Aramark Uniforms/Courtesy Chevrolet / Chevrolet | 128 | $1,020 | ||
| 25 | 6 | 7 | Harold Fair Jr. / Taylor, MI | Spicer/Fair Enterprises / Chevrolet | 94 | $1,010 | ||
| 26 | 3 | 35 | David Stremme / South Bend, IN | Industrial Safety and Environmental Services/AFCO / Pontiac | 81 | $1,000 | ||
| 27 | 15 | 11 | Jeff Lane / Knightstown, IN | Gas America/G.W. Pierce Parts/Ed Martin Auto / Chevrolet | 63 | $1,000 | ||
| 28 | 24 | 12 | Scott Neal / Middletown, IN | 4-Star Auto Place/Tire Barn / Chevrolet | 48 | $1,000 | ||
| 29 | 20 | 91 | Bobby Blount / Walkerton, IN | Medallion Tortilla Chips/Eagle Creek Aviation/Port City Racing / Chevrolet | 34 | $1,000 | ||
| 30 | 22 | 4 | Todd Oliver / Indianapolis, IN | Fuzzy Zoeller’s Barbeque Sauces / Chevrolet | 28 | $1,000 | ||
| 31 | 16 | 16 | Mike Bryant / Fort Wayne, IN | Franke Plating Works/ Dantzer Heating & Cooling / Oldsmobile | 7 | $1,000 | ||
| 32 | 28 | 94 | A.J. Bowlen / Bloomington, IN | Pennzoil Motor Oil/Roger’s Car Hospital / Chevrolet | 7 | $1,000 | ||
| Preceded by 1998 Winchester 400 |
1999 Winchester 400 Winner: Brian Ross |
Succeeded by 2000 Winchester 400 |