During the 2005–06 season, Maynard was loaned out to Witton Albion in January 2006, Maynard made a big impression at the non-league side, helping them to their most successful run of the season in the UniBond League. After returning to Crewe, Maynard continued to show fine form in the reserves side; by the end of the season, young Maynard made his Crewe début as a substitute for Michael Higdon in a 4–2 win over Millwall at the end of the 2005–06 season. He scored with his first touch in professional football, in front of Scouts representing 20 different clubs, after Michael O'Connor's shot hit the post. Eddie Johnson; Luke Varney and Steve Jones scored the other three goals for Crewe.
It seemed likely that Maynard would get his full début for Crewe during the 2006–07 season, with players such as Steve Jones leaving relegated Crewe for Championship side Burnley. However, some of Crewe's new signings, such as Ryan Lowe and the return of former player Rodney Jack, gave Maynard a bit of competition for a place in the first eleven. Maynard performed very well in his second year of professional football, forming a partnership with Varney where the two proved to be one of the most productive partnerships, in terms of goal scoring, in League One with a total of 33 league goals between them. During his first full season, the Englishman also picked up the "Player of the Month" award for September.
With Luke Varney gone after a £2 million transfer to Charlton Athletic, Maynard was seen as the club's main goalscoring threat. His second full season at the club, however, was brought to a stand still for four months after he suffered a bone fracture of his fibula and also damaged his ankle ligaments during the club's season opener against . In an interview with FourFourTwo magazine, Maynard admitted that he had "broke downa few times" during his four months of rehabilitation, although he would later recover and return to fitness and soon featured as a non-used substitute in an away match against before playing the second 45 minutes of the FA cup tie versus on December.
The striker struggled to score a goal during his first initial months back in the first team, with only two goals scored in his first two months back from injury. It wasn't until the following months of February and March that the young striker got back into form and soon showed his potential by scoring in seven consecutive games including a hat-trick at senior level, his first for the club, against relegation rivals , "I've scored a couple of doubles before" he said in an interview in 2008, "so I thought it was a long time coming. I got all the lads to sign the match ball for me." Crewe managed to avoid relegation for the second time in three seasons at the expense of , despite losing 4-1 to Oldham on the last day of the season. During the summer following the end of the season, Maynard was linked with a number of clubs including Premiership club .