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Now-senior guard Jonah Charles during last season's game against Temple at the Palestra on Dec. 4, 2021. Credit: Kylie Cooper

Penn men’s basketball will play 29 games this regular season, and though each game bears weight, five stand out above the rest as moments to define the 2022-23 campaign.

Nov. 7 @ Iona

Call it recency bias, but Penn’s season-opening matchup against the Gaels will be a vital measuring stick for the rest of its season. Led by legendary coach Rick Pitino, Iona comes in fresh off a 25-8 run last season that included victories over No. 10 Alabama and Ivy squads Harvard and Yale. If Penn wants to make a statement about the caliber of its team right off the bat, Monday’s contest in New Rochelle, N.Y. will serve the perfect chance.

Dec. 3 vs. La Salle

Last season, the Quakers delivered a putrid 0-4 in Big 5 play, dropping each of their matchups against their Philly rivals. Against La Salle, Penn can begin to right the ship, but that won’t be the only headline to highlight this game from the rest. In early April, the Explorers hired none other than Fran Dunphy, who coached Penn from 1989-2006, brought the Quakers to nine NCAA Tournaments, and is considered by many to be the greatest coach in Penn men's basketball history. In a Saturday afternoon matchup at the Palestra, Dunphy will be returning to coach at his old stomping grounds for the first time since January of 2018, when he led Temple’s program.

Jan. 16 vs. Princeton

Just two weeks into Ivy League play, the Quakers will confront the Princeton Tigers, a team which served defeat to Penn twice last season, and by double digits each time. Penn was ranked first in the Ivy League preseason media poll, and in assuming the position, the Quakers have to prove themselves against conference heavyweights like the Tigers to show that they deserve it. Princeton lost two of its three main scorers this offseason, but the team is still led by reigning Ivy League Player of the Year Tosan Evbuomwan.

Jan. 21 @ Yale

Last season’s run for Penn was halted by a heartbreaking 67-61 loss in the Ivy Tournament semifinal against the Yale Bulldogs. Over 10 months later, the Quakers will have the chance to avenge defeat, as they travel to New Haven, Conn. for a Saturday evening matchup. The Bulldogs will be without Azar Swain, their leading scorer during the 2021-22 campaign, who put up 25 of his team’s 67 points in the Ivy Tournament against Penn.

Feb. 11 @ Harvard

The peak of last season’s Penn team was arguably from late-January to mid-February, when the Quakers rattled off five consecutive Ivy wins — three of which were claimed on the road. The first of those away games was at Harvard, where, for the first time since 2012, Penn earned a win on the Crimson’s home floor. Against a defensively stout Harvard squad, Penn will have its hands full, but a win could be as big a momentum boost as it was last season to launch Penn toward the Ivy League Tournament.