Kevin Harvick sprinted around the outside of Richard Childress Racing team-mate Jeff Burton to claim victory in a green-white-chequered finish at Richmond.
The late-race caution, caused by Brian Vickers hitting the wall, denied Juan Pablo Montoya a near-certain first NASCAR Sprint Cup oval win.
Harvick was second, but seemed too far behind to challenge when Vickers lost control of his Joe Gibbs Racing Toyota. Both Montoya and Harvick, and Kurt Busch who ran a strong third for Furniture Row, opted to pit for fresh rubber.
Montoya restarted sixth, on the unfavoured outside line. From fifth Harvick bolted past the leading four cars who had stayed out on 60-lap old tyres.
Burton started from first, but was powerless to stop Harvick coming by, and fell to fifth by the flag.
Three of the fancied runners hit trouble when Tony Stewart got loose and tipped Jimmie Johnson into a spin (pictured below).
Kyle Busch found the track in front of him blocked, and ran into Johnson, causing heavy damage to the front of his Joe Gibbs Racing Toyota in the process.
Two more frontrunning cars fell out of contention not long after the race restarted when Mark Martin and Kasey Kahne tangled. And in an ill-tempered final quarter of the race, Martin Truex Jr was spun out of second by Kurt Busch.
Reigning Cup champion Brad Keselowski's hopes of repeating his Nationwide success ended when his Penske Ford - running in unusual red livery - brushed the wall when he suffered a right-front puncture.
Smart pitwork kept him on the lead lap, but he was ultimately black-flagged for failing to keep up the minimum speed.
During the fraught final two laps there was plenty of argy-bargy, particularly involving Kurt Busch, Matt Kenseth, who dominated the first half of the race, and Stewart.
This carried on to the 'cool-down' lap as Busch rammed Kenseth and Stewart squeezed Busch into the wall.
Clint Bowyer used his fresh tyres to sprint into second, while Joey Logano took third. Montoya eventually came home fourth and was left to rue what could have been.
Results - 406 laps (green-white-chequered finish): Pos Driver Team/Car Time/Gap 1. Kevin Harvick Childress Chevrolet 3h18m17.000s 2. Clint Bowyer Waltrip Toyota + 0.343s 3. Joey Logano Penske Ford + 0.946s 4. Juan Pablo Montoya Earnhardt Ganassi Chevrolet + 1.549s 5. Jeff Burton Childress Chevrolet + 1.558s 6. Carl Edwards Roush Fenway Ford + 1.742s 7. Matt Kenseth Joe Gibbs Toyota + 2.190s 8. Aric Almirola Petty Ford + 2.340s 9. Kurt Busch Furniture Row Chevrolet + 2.371s 10. Dale Earnhardt Jr Hendrick Chevrolet + 2.615s 11. Jeff Gordon Hendrick Chevrolet + 2.732s 12. Jimmie Johnson Hendrick Chevrolet + 2.765s 13. Paul Menard Childress Chevrolet + 2.900s 14. AJ Allmendinger Phoenix Chevrolet + 3.055s 15. Ryan Newman Stewart-Haas Chevrolet + 3.138s 16. Ricky Stenhouse Jr Roush Fenway Ford + 3.242s 17. Martin Truex Jr Waltrip Toyota + 3.416s 18. Tony Stewart Stewart-Haas Chevrolet + 3.497s 19. Bobby Labonte JTG Daugherty Toyota + 3.637s 20. David Ragan Front Row Ford + 3.673s 21. Kasey Kahne Hendrick Chevrolet + 3.887s 22. David Reutimann BK Toyota + 3.949s 23. Dave Blaney Baldwin Chevrolet + 4.153s 24. Kyle Busch Joe Gibbs Toyota + 4.636s 25. Landon Cassill Circle Sport Chevrolet + 4.657s 26. Jamie McMurray Earnhardt Ganassi Chevrolet + 5.525s 27. David Gilliland Front Row Ford + 1 lap 28. Josh Wise Front Row Ford + 2 laps 29. Danica Patrick Stewart-Haas Chevrolet + 4 laps 30. Casey Mears Germain Ford + 4 laps 31. David Stremme Swan Toyota + 4 laps 32. JJ Yeley Baldwin Chevrolet + 5 laps 33. Brad Keselowski Penske Ford + 7 laps 34. Timmy Hill FAS Lane Ford + 9 laps 35. Brian Vickers Joe Gibbs Toyota + 14 laps* 36. Greg Biffle Roush Fenway Ford + 15 laps 37. Travis Kvapil BK Toyota + 38 laps 38. Mark Martin Waltrip Toyota + 57 laps * Not running at finish Retirements: Joe Nemechek NEMCO-JRR Toyota 245 laps Brian Keselowski Keselowski Toyota 186 laps Michael McDowell Parsons Ford 121 laps Marcos Ambrose Petty Ford 109 laps Mike Bliss Humphrey Smith Toyota 17 laps