The 2008 Daytona 500 was the 50th annual running of the event. It was held on February 17, 2008 at Daytona International Speedway in Daytona Beach, Florida. The race was the 50th to be run since the first in 1959, won by Lee Petty. To commemorate the event, the Harley J. Earl Trophy, which goes to the winner of the race, was plated in gold instead of silver. In addition, the winning car was placed on display for one year at the Daytona 500 Experience attraction just outside Turn Four. Ryan Newman won the race, his only win in the 2008 season.

The 2007 Daytona 500, the 49th running of the event, was the first race of the 2007 NASCAR Nextel Cup Series season, taking place on February 18, 2007, at Daytona International Speedway in Daytona Beach, Florida. Kevin Harvick won the race by 0.02 second over Mark Martin in the closest finish since the first race at Daytona International Speedway when it took three days to declare Lee Petty the winner in 1959. The race was decided by a green-white-checker finish for the third year in a row, with two extra laps added for a total of 202 laps and 505 miles (813 km).

The 2006 Daytona 500, the 48th running of the event, was the first race in the 2006 NASCAR Nextel Cup season. It was held on February 19, 2006 at Daytona International Speedway in Daytona Beach, Florida. Jimmie Johnson won the race in a green-white-checker finish. It was the second Daytona 500 in a row to go longer than 200 laps and 500 miles (800 km); this race, like the previous Daytona 500, had a total distance of 203 laps and 507.5 miles (816.7 km). This was also the first Daytona 500 to end after dark, ending even later than the 2005 race, in which the checkered flag had waved just a few moments after sunset.

Johnson's car failed pre-race inspection and as a result his crew chief, Chad Knaus was suspended for the first four races and the team was fined $200,000. As a result, Darian Grubb replaced him as crew chief. Knaus was not blocked, however, from contacting the team and by many accounts still had significant input. Johnson would go on to win his first championship that year.

The 2005 Daytona 500, the 47th running of the event, was held on February 20, 2005 at Daytona International Speedway in Daytona Beach, Florida as the first race of the 2005 NASCAR Nextel Cup season. Dale Jarrett won the pole and Jeff Gordon won the race, making this his third Daytona 500 win. Kurt Busch finished second[2] and Dale Earnhardt, Jr. finished third.[2]

As the result of NASCAR's implementation of the green-white-checker finish rule the previous season, the race had three extra laps due to a caution with three laps to go, reaching a total distance of 203 laps and 507.5 miles (816.7 km). Because of that, this was the first Daytona 500 to go longer than 500 miles. It was also the first Daytona 500 to end at sunset, around 6:18 pm EST.

A crowd of 200,000 people were estimated to have attended this race.

The 2004 Daytona 500, the 46th running of the event, was the first race of the 2004 NASCAR Nextel Cup season. It was race held on February 15, 2004 at Daytona International Speedway in Daytona Beach, Florida. The race was televised by NBC, with Allen Bestwick, 1975 race winner Benny Parsons, and Wally Dallenbach, Jr. calling the action for the second time after the 2002 race. It was the first NASCAR Nextel Cup race to air in high definition.

Dale Earnhardt, Jr. won the race, making this his first Daytona 500 victory exactly six years to the day after his father Dale Earnhardt, Sr. won his first and only Daytona 500 in the 1998 race. Tony Stewart finished second and rookie Scott Wimmer finished third.

The 2003 Daytona 500, the 45th running of the event, was the first race of the 2003 NASCAR Winston Cup season, having been held on February 16 at Daytona International Speedway in Daytona Beach, Florida. 2000 NASCAR Busch Series champion Jeff Green won his second career Winston Cup pole.

Prior to the race, the drivers paid tribute by having decals on their cars in honor of the astronauts who were killed in the Space Shuttle Columbia disaster two weeks earlier, similar to the 1986 Daytona 500, in which they paid tribute to the fallen crew members of the Space Shuttle Challenger disaster.

The race ended after 109 laps when rain had begun pouring on the track. Michael Waltrip won the race for the second time in three years, giving him his third NASCAR Winston Cup win; all of his wins to that point had been in races held at Daytona. It was the first of Waltrip's two wins in 2003, both coming in restrictor plate races (he later won the EA Sports 500 at Talladega in October for his fourth and last Cup win). For the first time since 1966, the race was stopped due to rain; at 272.5 miles, this was the shortest Daytona 500 ever.

In the race, Ryan Newman had a wild accident in the tri-oval, where his No. 12 Dodge tumbled end-over-end. He was not injured in the crash. Following the incident, both Penske Racing and new manufacturer Dodge were investigated because of the quality of the car.

The 2002 Daytona 500, the 44th running of the event, was held on February 17 at Daytona International Speedway in Daytona Beach, Florida as the first of 36 races of the 2002 Winston Cup Season. Rookie Jimmie Johnson, driving the No. 48 Chevrolet for Hendrick Motorsports, won the pole with fellow Daytona 500 rookie Kevin Harvick qualifying second, making this the first time the field would be led by two first-time Daytona 500 participants. Ward Burton, driving the No.22 Dodge for Bill Davis Racing, won the race. This race was the last for long-time veteran driver Dave Marcis.

As part of the television contract signed at the end of the 2000 NASCAR season, the 2002 Daytona 500 was televised by NBC. Allen Bestwick provided the play-by-play in the booth with color commentators Benny Parsons and Wally Dallenbach, Jr. The prerace show was hosted by Bill Weber, who reported from the pits with Matt Yocum, Marty Snider, and Dave Burns. This was the first time NBC televised the Daytona 500.

The 2001 Daytona 500, the 43rd running of the event, was the first race of the 2001 NASCAR Winston Cup Series schedule. It was held on February 18, 2001 at Daytona International Speedway in Daytona Beach, Florida, consisting of 200 laps and 500 miles on the 2.5-mile (4 km) asphalt tri-oval. The race was the first ever Winston Cup telecast shown by the Fox network, which had received broadcasting rights along with NBC at the end of the previous season, replacing the two former NASCAR broadcasting channels CBS and ESPN. Bill Elliott won the pole and Michael Waltrip, in his first race in the No. 15 car for Dale Earnhardt, Inc., won the race. This was the first Winston Cup victory of his career, coming in his 463rd start, the longest wait for a first win. His teammate Dale Earnhardt Jr. finished second and Rusty Wallace finished third.

On the final lap, a major accident was triggered by 1998 Daytona 500 winner and seven-time series champion Dale Earnhardt losing control of his car and collecting Ken Schrader in a head-on collision with the outside retaining wall in turn 4. Three cars were involved in the crash, which killed Earnhardt instantly.[3] The race was also marred by an 18-car pile-up on lap 173 that began when Ward Burton made contact with Robby Gordon, sending Tony Stewart flipping twice down the backstretch. After Earnhardt's death (as well as other notable deaths of other drivers in other NASCAR national touring series in the previous season), NASCAR implemented rigorous safety improvements in later seasons.

The 2000 Daytona 500, the 42nd running of the event, was held February 20 at Daytona International Speedway, in Daytona Beach, Florida as the first race of both the 2000 NASCAR Winson Cup season and the 2000s decade. Dale Jarrett, the polesitter, led the most laps and won the race for the third time, after winning in 1993 and 1996. This was (to date) the last Daytona 500 to be televised by CBS and thus the last 500 broadcast for Buddy Baker and Ned Jarrett. Dave Marcis failed to qualify for the first time since 1968.

The average green flag run for the race was confirmed by NASCAR officials as 29 laps. 12% of the event was held under a caution flag, mostly for oil, debris, and accidents.

The green flag waved at 12:15 pm as pole-sitter Dale Jarrett led the field to the start of the race. However, he did not lead until lap 5 since he lost the first lap to outside polesitter Ricky Rudd. Mike Skinner took the lead away from Rudd on lap 2 and led two more. Bill Elliott briefly took the lead on lap 34, and then Jarrett regained it just before the first caution came out due to oil on a section of the track. The next green flag period lasted nearly 100 laps, in which Mark Martin took the lead and remained there for 65 laps. The second caution (also for oil) came on lap 134 and the third one came out on lap 157. During the latter caution, Johnny Benson, Jr. passed Martin for the lead as the lead-lap cars raced back to the yellow flag.

Benson, Jr. led the next 39 laps, which included yet another caution on lap 170, once again for oil. On lap 192, several drivers, including Michael Waltrip, Elliott Sadler, and John Andretti, were involved in a crash right at the start-finish line. The race restarted with four laps to go, and Benson, Jr. looked as if he might capture his first cup series win in the biggest event of the season when the Fords of Jarrett and Jeff Burton ganged up on and passed him entering turn 3. One lap before the white flag was scheduled, Jimmy Spencer hit the front stretch wall, which allowed the final lap to be run under caution, securing a third Daytona 500 win for Jarrett, making him the fourth driver to win three or more Daytona 500s.

The 1999 Daytona 500, the 41st running of the event, was held February 14, 1999, at Daytona International Speedway. Jeff Gordon won the pole and won the race, making him the first Daytona 500 pole sitter to win the race since Bill Elliott in 1987

This race was known for Jeff Gordon's daring three-wide pass on Rusty Wallace and Mike Skinner. He passed Wallace after ducking to the apron, nearly plowing into the damaged car of Ricky Rudd. Skinner jumped to the outside and they raced three-wide for three laps until Dale Earnhardt (the defending Daytona 500 winner) gave Gordon the needed push. The race was also known for a determined Earnhardt repeatedly trying to pass Gordon for the lead on the final lap, only for Gordon to beat him to the finish. The race had a 13-car pileup on lap 135, in which eventual series champion Dale Jarrett flipped over twice but however, he was uninjured.