Disclosed is a system for cutting chewing gum. The system comprises a conveyor (4) configured to provide a chewing gum sheet to at least one rotary type cutting device (6,7,8,9). The rotary type cutting device (6,7,8,9) including at least one cutting surface configured to score said chewing gum sheet to a depth less than the entire height of the chewing gum to form a gum web of chewing gum and/or to cut through the entire height of the chewing gum sheet to form separate portions of chewing gum. The system further comprises a compressed air delivery unit (20) and an exit conveyor (5) configured to transport said chewing gum from the system. The compressed air delivery unit (20) is configured to facilitate release of chewing gum from said at least one rotary type cutting device (6,7,8,9) by applying compressed air to said at least one rotary type cutting device in a direction that is generally opposite rotation of said rotary type cutting device (6,7,8,9).