VVV Venlo failed to preserve their Eredivisie status following a 2-0 promotion-relegation play-off defeat against ADO Den Haag on Wednesday.
VVV finished the season second from bottom in the Eredivisie, however their relegation was not confirmed until their failure to negotiate the play-offs.
And their path through the play-off system was halted by ADO in the deciding game of their three-match series to ensure they will play in the Dutch second tier next season.
ADO took a 19th minute lead when Ken Leemans put the ball into his own net, before Daryl Janmaat sealed VVV's fate 10 minutes from time.
The defeat may be made easier to stomach for VVV boss Andre Wetzel who will join ADO next season.
ADO will play RKC Waalwijk in the next round of the play-offs after they easily defeated MVV Maastricht 4-0.
RKC jumped out to a two-goal lead after 15 minutes with Tim Peters and Fred Benson on target before Martijn Reuser scored a double to complete the win.
FC Zwolle will play De Graafschap in the other play-off after Antonio Toze score the only goal of the game against FC Den Bosch
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