Milan have not activated an option to buy for 10 years, but could break that negative streak to sign Tiemoue Bakayoko from Chelsea.
The midfielder arrived on a one-season loan for €5m with option to buy in June 2019 for another €38-40m.
Coach Gennaro Gattuso has helped him develop immensely and made no secret of his desire to keep the 24-year-old on a permanent basis.
However, this would be something of a freak occurrence, as calcionews24.com calculated that Milan have not taken up a single option to buy in the last decade.
That is a run of 18 different players who arrived on loan with an option to buy and did not remain past the temporary deadline.
These names over the years include Mario Balotelli, David Beckham, Mattia Destro, Bojan Krkic, Gerard Deulofeu, Lucas Ocampos, Mario Pasalic, Andriy Shevchenko, Adel Taarabt and most recently Gonzalo Higuain.
In fact, Higuain was released six months early into his loan spell from Juventus, in order to join Chelsea instead.