2. Patrick Ewing/Charles Oakley, New York Knicks
The two biggest market teams in the East had a lot of instant classic playoff series throughout the 1990’s. The Chicago Bulls and the Knicks even had a few rivalry showdowns that stemmed from the 1980’s all the way through the early 2010’s.
Up to the point where Rose and Noah were taking on former Knicks star forward Carmelo Anthony in the early 2010’s, the Bulls had a huge rivalry with New York’s biggest team. But the most memorable of this rivalry came throughout the 1990’s, mostly early in that decade.
The Bulls met with the Knicks in the playoffs on five different occasions in the 1990’s. And the two biggest stars for the Knicks that were a thorn in the side of the Bulls were big men Patrick Ewing and Charles Oakley. The latter of the two had some of his worst per game averages against any one player/team against Jordan and the Bulls (nine points per game and 10 rebounds).
Jordan largely dominated Ewing and Oakley. But the Knicks did get the best of the Bulls in one playoff series when MJ was out of the NBA, playing in the Chicago White Sox minor league organization with the Birmingham Barons. He had a record of 30-13 in the regular season against Ewing and a record of 23-7 against Oakley.
Even when the Knicks made it past the Bulls in the 1994 Eastern Conference Finals, they still couldn’t claim a title. They lost in the NBA Finals in 1994 to the Houston Rockets.