Bosz's first meeting with Ajax as a trainer of a rival team was on 7 December 2002, when he was in charge of De Graafschap. The match ended in a 1-1 draw, with De Graafschap holding Ajax to a stalemate. VoetbalPrimeur reports that Bosz has faced Ajax 22 times as a trainer, with his teams winning just four times. They have also drawn seven times and lost 11 times, scoring 30 goals and conceding 54.
Bosz's teams have managed to win twice against Ajax as the head coach of Vitesse in the Johan Cruijff ArenA. However, as the PSV trainer, he has never won against Ajax on their home turf in Amsterdam.