 Mark and the Valvoline/Cummins team had another successful NASCAR Winston Cup season in 1999. The season started out on a high note when Mark won the Bud Shootout at Daytona International Speedway. The win was Mark's first in a Winston Cup car on the 2.5-mile superspeedway. One week later, Mark started the Daytona 500 in ninth place, but finished in 31st place after he was involved in a 12-car accident. Once again, Mark had to dig himself out of a hole to begin the point season. He made up a lot of ground the following weekend at North Carolina Speedway where he visited its Victory Lane for the first time since 1989. The win boosted him from 31st in the point standings all the way up to eighth place. Strong top 10 finishes followed at Las Vegas, Atlanta and Darlington, which left Mark sitting in fourth place. His luck changed at Texas when he blew a right front tire while leading the race. The crew spent 80 laps repairing the damage. Mark returned to the track, but finished a disappointing 34th. The poor finish dropped him back to sixth in the points. |
 The Valvoline/Cummins team picked up the pace in April with three top five finishes in three races. Mark challenged Rusty Wallace for the win at Bristol, but had to settle for second place. He finished fifth at Martinsville and third at Talladega. By the end of the month, he was third in the Winston Cup points and climbing fast. Mark had a slight setback in his quest for a championship at California. After starting third based on points, Mark ran with the leaders all day until his engine gave up on lap 196 of 250. The early end to his day gave him a 38th place finish and moved him back to fifth in the points, 205 points behind the leader. |
| The Richmond race in May started a string of great finishes for Mark. In the next six races, Mark earned five top five finishes and finished in the top 10 in all six events. He was third in the point standings at the end of the first half of the season. |
 In July, the team returned to Daytona to start the second half of the season. Mark took the car that he considered the best restrictor plate car he had ever driven. It was the same car that won the Bud Shootout and finished third at Talladega. He qualified third for the Pepsi 400 and was strong in the final "Happy Hour" practice Friday night until he cut a right front tire, which sent him into the wall on the backstretch. The car sustained heavy damage and the team was forced to roll out the backup car. |
| Mark suffered a fractured left wrist, rib and broke the tibia plateau in his left knee, which would require surgery later in the week. Despite his injuries, Mark raced the next evening and finished 17th in the backup car. |
| Only two days after his knee surgery, Mark climbed back into his Valvoline/Cummins Taurus to qualify at New Hampshire. He was forced to take his first and only provisional of the year and started 37th. Amazingly, Mark drove the entire race and finished in sixth place to retain his third place in the points. A third place finish at Pocono the following week moved him up to second in the points, trailing Dale Jarrett by 254 points. |
 The month of August was strong for Mark, as he posted four top 10 finishes at Indianapolis, Watkins Glen, Michigan and Bristol. September started out well with a fourth place finish at Darlington. Things took a turn for the worse under the lights at Richmond the following week. Mark's night ended early when smoke began to spew from the car on lap 366 of 400. He finished 35th. The next week at New Hampshire was not much better. He was involved in an accident on the fifth lap of the race and then again on lap 126. There was damage to the suspension, and Martin finished in 17th place, one lap down to the leaders. The month ended up great with a win at Dover. The crew brought back the same car that won in 1998, and Martin led 161 of 400 laps en route to his second victory of the season. The win boosted him back up to second in the point standings, but he trailed Jarrett by 257 points. |
 The month of October brought Mark two more top 10 finishes at Charlotte and Rockingham, but more importantly, it brought Mark his only Winston Cup pole of the year. Mark set the qualifying mark at North Carolina Speedway with a speed of 157.383 mph to earn a position in next year's Bud Shootout at Daytona. The Valvoline/Cummins team rounded out the season with three more top five finishes at Phoenix, Homestead and Atlanta in November. Mark ended the year third in the Winston Cup point standings, behind Dale Jarrett and Bobby Labonte. Mark finished the 1999 season with two wins, 19 top five and 26 top 10 finishes. He earned $2,783,296 and finished in the top six in points for the 11th consecutive year. |
| "We had a great season," Mark said. "We may not have won as many races as we did last year, but the effort on this team was as great as ever. My team supported me through all of my injuries and never once doubted my ability as a driver. I am already looking forward to next year and believe we can do even better." |