Despite a win at Loudon in 2005, Crawford finished seventeenth in points, mainly due to missing the first race of his Truck career after suffering injuries, ironically while practicing for the Built Ford Tough 225. Boris Said, who was scheduled to be a guest on the Speed Channel's race coverage, was hired to drive the truck. While he wrecked later in the race, he returned to the booth to cover the rest of the race, as the late Neil Bonnett once did at Talladega Superspeedway in 1993 after taking a wild ride into the tri-oval. He did score two poles at Atlanta and Martinsville and had 11 top tens and 3 top fives. For the 2006 season Crawford had five top-fives and thirteen top-ten finishes including a win on August 4 at O'Reilly Raceway Park, finishing 9th in the final standings, the win at O’Reilly was his final career victory. Rick had a consistent year in 2007 racking up 11 top 5 finishes, 18 top 10s and a near win at Mansfield Motorsports Park en route to a 5th place standing in the points championship. The eighteen top ten finishes would be a career high to date. In 2008 Crawford put together another solid season with thirteen top tens and seven top fives and a pole at Texas. He would end the season seventh in points. In 2009, now age 50, Crawford would again finish in the top ten in points at 10th. He scored seven top tens and three top fives and would win the pole at Martinsville for the second time in his career. Crawford would start the 2010 season with a great deal of uncertainty. Longtime sponsor Circle Bar Motel and RV Park would cut back their sponsorship of the team dramatically and Crawford stated that he was unsure how many races they would be able to run without a new sponsor. He would run the first four races of the season with Circle Bar, scoring two top tens. However, prior to Kansas Crawford announced that he would not race for Circle Bar in the #14 truck and would instead race in the Ray Hackett Racing #76 truck with sponsorship from SUPERSEAL Construction Products. This would be the first race in his record 327 Camping World Truck Series starts that he would not be in the #14 and would not be racing under Circle Bar Racing. Crawford would qualify for that race 15th and finish 31st after an accident going for the lead. In August, Crawford would take yet another unfamiliar step in his career as he would join forces with Tagsby Racing to race in the EnjoyIllinois.com 225 at Chicagoland Speedway.