 He struggled to nail down a starting spot in the team during his first season at the club, particularly during the reign of Mark Robins, although he went on to make 35 appearances and scored three times.The arrival of Steven Pressley as Coventry City manager in March 2013 saw Fleck regain a starting spot in the Coventry City line-up, starting every game of the remaining 2012–13 season in a deep-lying central midfield role.Fleck remained first-choice for the following season which Coventry City played at Northampton Town's Sixfields Stadium and played a key role in the team as they overcame a 10-point deduction to mount an unlikely play-off push for the first half of the season.