A work vehicle cooperation system includes: a master traveling track calculation unit that calculates a traveling track of a master work vehicle (1P) based on a position of the master work vehicle (1P) a loop traveling detection unit that detects loop traveling in a loop work area (B), which is defined as the perimeter of a U-turn work area (A), the U-turn work area (A) being an area in which work is performed by repeating straight work traveling and U-turns a redirection traveling target calculation unit that calculates a redirection traveling start point and a redirection traveling end point (Pc3) of a slave work vehicle (1C) based on a redirection traveling track including a redirection traveling start point (Pp1) and a redirection traveling end point of redirection traveling of the master work vehicle (1P) and a loop work traveling target calculation unit that calculates a target traveling position in loop work traveling of the slave work vehicle (1C) from the redirection traveling end point (Pc3) to a next redirection traveling start point (Pc1), based on the work widths of the master work vehicle (1P) and the slave work vehicle (1C), and a loop work traveling track of the master work vehicle (1P).