Edmonton Oilers History By joelpeterman Period: Oct 1, 1979 to Nov 15, 1988 History of the Edmonton Oilers Oct 9, 1979 Oilers enter the NHL Apr 1, 1981 Oilers first playoff series win! Apr 15, 1984 Oilers win first stantley cup! Stanley Cup Apr 3, 1986 Oilers win first Presidents Trophy! Aug 9, 1988 Oilers Trade Wayne Gretzky "The Trade"