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During the 1999 season, the Quakers upset No. 7 Temple and would be crowned as Ivy League champions by the end of the season.

Credit: DP Archives

The legendary winning streak. Black Tuesday, one of the most infamous events in Penn’s athletic history. The hoisting of the Ivy League Championship trophy. Getting into the dance. All of it was a part of the 1998-1999 Penn men's basketball season.

Coming off a tough losing streak against the Princeton Tigers and no Ivy League titles in the previous three years, the Quakers knew that something had to change.

Sure, they had kept things competitive. The Penn and Princeton basketball teams had each been either winning or sharing the Ivy League Championship since 1963 (save for 1986 and 1988). In fact, many even considered the Quakers to be possible March Madness early upsets.

However, Penn Basketball was falling short on expectations for the latter part of the decade, and the fans in the Palestra knew that they were due for a championship. Coach Fran Dunphy knew this, and he was ready to provide.

Starting off the season against basketball powerhouse Kansas, a loss was expected. However, Penn kept it surprisingly close despite losing by a final score of 61-56, which raised expectations for the game against Big Five rival Temple, who ranked No. 8 in the nation.

Then came the miracle, and with it the magic of the Palestra was back.

This game would go down as one of the biggest upsets in Penn basketball history, with the Quakers taking the win in overtime, 73-70. Star guard Michael Jordan, as if taken over by the legend with the same name, put up a staggering 22 points to lead his team to the historic upset.

Penn then split its next 4 games with a 2-2 record, and were able to notch some impressive wins against some respectable teams in Lehigh and Iona. Shortly after, what really got the attention of fans was the 11-game winning streak against Philly Big Five and Ivy League opponents.

When looking at the scores, it’s easy to see just how dominant the Red and Blue were that year. Wins such as 86-55 against Brown, 66-58 against St. Joseph’s, 86-62 against Cornell, and a staggering 81-56 against Harvard put the Quakers into the championship conversation.

Then came Black Tuesday.

The game, which the DP recently rehashed, was arguably one of the worst nights to be a Quaker fan. To sum it up the Tigers beat the Quakers by a score of 50-49 due to an 18-point comeback in the second half. It was a devastating loss that is still remembered vividly by many involved to this day. 

“At the time, that game was a really hard game to lose,” said Steve Donahue, also a coach at Penn from 1990 to 2000. “That team was resilient though, and it says a lot about a team if you can turn around and win 21 straight Ivy games.”

And that’s just what the team did. No other Ancient Eight team could beat the Quakers that year, and the team only took one more loss against long-time basketball powerhouse Villanova.

The fateful rematch against Princeton went the right way this time, with Penn stomping the Orange and Black in the conference championship by a score of 73-48. This win would nab the Quakers a No. 11 seed in the 1999 March Madness bracket. This was an incredibly impressive feat, even though the team would go on to lose the first round against the SEC champion Florida Gators, a team that would make it to the Sweet Sixteen.

The team is best remembered for getting over the hump of Princeton and kickstarting another run of dominance that would last for nearly a decade. 

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