With the original home of Penn Basketball proving to be highly inadequate in size, university officials pushed for larger facility to play and watch basketball. In 1925, the Chairman of the Council of Athletics, Sydney Hutchinson was persuaded, and plans were put into motion. The new gym would include seating for 10,000 – the upper half of which would be permanent, while the lower half would roll under in order to accommodate additional practice space. The proposal, location and funds didn't take long to be approved and construction officially began in 1926.

From there, all that was left was to give the new building a name. University officials discussed options such as "Coliseum" or "Arena," but were ultimately rejected for being too ordinary. Professor of Greek, Doctor William N. Bates suggested The Palestra – a rectangular enclosure attached to a gymnasium where athletes would compete in various sports in front of an audience. The name was widely accepted by the organizing committee as it met all of their specifications: authentic, dignified, descriptive, and novel. On January 1, 1927, The Palestra officially opened its doors.

The Palestra has received the standard upgrades over the years, including refurbishments to the hardwood court and installation of new seating to the lower sections. More notable is the addition of the upper-north press area, which was built over the existing bench seating in the upper-most sideline. In 2000, the concourse walls were converted into a museum, celebrating the history of basketball in Philadelphia. An ode to the Big 5 can be found at the west-end, just inside the main lobby. The south concourse highlights all things Penn men's and women's basketball, while the north side features notable coaches, opponents, and high school stars who have played on The Palestra floor. Finally, the east-end houses tributes to Penn wrestling and volleyball, the Ivy League, famed broadcasters and journalists, and some of the buildings most memorable moments.

A state-of-the-art sound system, fixed digit scoreboard, LED videoboard and climate-controlled server room was installed in 2011, giving the stadium a much-needed technology boost. In 2018, Penn Athletics entered into a partnership with Macquarie Investment Management, providing exclusive naming rights and renaming it to "Macquarie Court at The Palestra." Today, the once 10,000 seat stadium holds a maximum capacity of 8,722. However, The Palestra is still famed for its close-to-the-court seating, with the bleachers ending at the floor and no barrier between the fans and the action. While improvements have been made in order to keep the building modern and operational, The Palestra remains virtually unaltered to this day.

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On January 1, 1927, the Quakers rang in the New Year with the Grand Opening of The Palestra and a 26-25 win over Yale in their new home. A total of 10,000 people were estimated to be in attendance that day – the largest crowd to attend a basketball game on the east coast at the time. However, this wasn't the first the team took the court at The Palestra. Two days prior, Penn Basketball took on Pennsylvania Military College (now Widener University) in an exhibition game and christened the cathedral with a 21-17 win. The Palestra welcomed a new tenant in 1970, as the Penn Women's Basketball team began their inaugural season.

The Palestra has hosted more visiting teams than any other arena in the country and with a home like that, there's no doubt that the Quakers have hosted some impressive opponents over the years. Kentucky, Kansas, North Carolina, Duke, Syracuse and a plethora of the NCAAs top men's basketball programs have all competed against Penn at The Palestra. In addition, the Penn women have also hosted several notable opponents, including Notre Dame, Duke and more.

Penn Basketball has established many traditions throughout its history, many taking place in The Palestra. Although they don't play each other every year, the meetings between Penn and Drexel are known as the Battle of 33^rd Street. The rivalry is fueled by the proximity of the schools, as the campuses share a border. While the tradition began prior to 1927, a majority of the games were held consistently at The Palestra following its construction. However, the most prominent tradition was the formation of the Big 5, the infamous city series between Penn and four other Philadelphia universities – La Salle, Saint Joseph's, Temple and Villanova. Its thanks to the Big 5 that Penn Basketball was able to adopt its own modern version of the streamer toss. Instead of tossing them after the first points scored, students and fans throw streamers onto the court after the band finishes their postgame rendition of the Red and the Blue.

The recent success of the Penn Women's Basketballs team has brought several postseason opportunities to The Palestra. In 2013, the opening rounds of the Women's Basketball Invitational (WBI) were hosted in University City. The Quakers defeated Howard and Fairfield in the first and second rounds. The Women's National Invitation Tournament (WNIT) has also made several appearances at The Palestra:
 

	Year	Round	Opponent	Final Score	W/L
	2015	Regional Semi	Hofstra Temple	65 - 58 61 - 56	W L
	2018	First Round	UAlbany	76 - 61	W
	2019	First Round	American	64 - 45	W

 
In addition to postseason, both teams hosted the occasional regular season tournament. The men hosted the Quaker City Tourney in 1961, 1964, 1967 and 1973, as well as the Josten's Classic in 1985 and 1988. The women put on the Penn Holiday Invitational during the 1980 and 1981 seasons, in addition to the 1986 Palestra Tournament.

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On November 23, 1954, University of Pennsylvania President, Dr. Gaylord Harnwell announced the formation of an informal association between five of Philadelphia's storied college basketball programs – La Salle University, Saint Joseph's University, Temple University, the University of Pennsylvania and Villanova University. Thus, "The Big 5" was born. With the creation of this intense intra-city rivalry, The Palestra became the official home of Big 5 basketball. In the heyday of the Big 5, all games were held in The Palestra and were often scheduled as double or tripleheaders, showcasing some of the city's best basketball talent. The schools agreed to split the series' ticket and concessions revenue equally after Penn was reimbursed for the building's upkeep and operational costs. As the Big 5 evolved and the women's basketball programs of each school grew, the group eventually expanded the series to include the women's teams.

From rollouts to streamers, several notable traditions came from the introduction of the Big 5 and began in the Palestra. As each team scored their first points, fans would toss streamers (in their school colors) onto the court. By 1985, schools outside of the Big 5 picked up on the tradition and began throwing streamers, as well as heavier, more dangerous objects. In response, the NCAA banned the tradition and teams that continued participating would be issued a technical. However, streamers still occasionally find their way onto the court – most frequently after a Penn Basketball home win. In addition to streamers, the student sections would often create large, hand-drawn banners, also known as "rollouts." In the spirit of friendly competition, each rollout contained witty messages aimed to support their teams while also taking shots at their opponents. The Palestra has also been the site of traditions born amongst its member schools. On December 3, 1955, the Saint Joseph's Hawk made his debut at The Palestra. The Hawk hasn't missed a Saint Joseph's men's basketball game since.

In November 2002, Associated Press sportswriter, Robert S. Lyons published Palestra Pandemonium: A History of the Big Five. Lyons chronicles the rich history, famed traditions, and intense rivalries of the Big 5. The book features interviews with players, coaches and administrators, as well as classic photos of the city series played in The Palestra. On January 18, 2014, ESPN's College Gameday visited The Palestra as La Salle took on Temple in a traditional Big 5 competition. The game concluded ESPN's "My Home Court" initiative – a week-long celebration of college basketball's greatest venues.

In the modern era of college basketball, the agreement amongst the Big 5 schools has evolved. While The Palestra is still considered the exclusive home of the Big 5, the participating schools shifted their series home games to their respective campuses in 1986. Villanova briefly withdrew from the series from 1991 only to return in 1999. Today, the Big 5 continues the round robin competition to declare a city champion. In addition, each of the schools still occasionally schedule a Big 5 home game at The Palestra, keeping the tradition alive.

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