While today Pittsburgh, like most major cities, is solidly in the Democratic column, that was not always the case. At the turn of the 20th century, for instance, Steel City decisively voted for William McKinley (R) over William Jennings Bryan (D) by 40.6%. McKinley won most of the city, often by large margins, with Bryan relegated to victories along the banks of the Allegheny and Monongahela Rivers.
However, despite McKinley improving on his performance against Bryan four years prior on a national level, his margin of victory in Pittsburgh was slightly less than the 42.2% margin he won the city with in 1896. Unfortunately, information on elections 25 years ago is hard to come by, let alone those held 125 years ago, and so I cannot say why McKinley did slightly worse.
This was the last election for PA-20, as the district was dismantled in redistricting following the 2000 census.
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2006 was an abysmal night for Pennsylvania's congressional Republicans, as the party lost one of the state's seats in the US Senate and four seats in the US House. One such seat was PA-04, anchored around the Pittsburgh suburbs, which had been represented by Melissa Hart (R) since 2000. Prior to the 2006 election, Hart had been seen as a rising star in Republican politics, notable for her ability to win despite the district favoring Democrats in terms of party registration.
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Despite a blue wave sweeping the country in 2008, Democrats did still see some losses in right-trending rural areas. Pennsylvania was no exception, as Barack Obama (D) lost three counties in the presidential race that John Kerry (D) had won four years earlier. These effects were felt down ballot as well, such as in rural HD-75, which had been represented by Dan Surra (D) since 1991. Despite Democrats making gains in the statehouse as a whole, the centrist legislator and Democratic caucus administrator was defeated by 25-year-old Matt Gabler (R), an Army Reserve captain. Gabler's campaign was bolstered by the backing of retiring US Representative John Peterson (R), which allowed Gabler to upset Surra by roughly 1,500 votes. Surra did best in the northern and southern townships of Elk County, as well as Johnsonsburg, but it wasn't enough to overcome Gabler's performance in Clearfield County and central Elk County. Gabler was re-elected for several more terms, receiving over 70% of the vote each time, before he retired in 2020.
The election was held due to then-mayor Bill Courtright resigning after entering a plea agreement regarding federal corruption charges. Upon her victory, Cognetti became Scranton's first female mayor.
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Dermody was the highest-level Democrat to lose re-election since Democratic Whip Mike Veon (HD-14) was defeated in 2006.
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In 2022, Pennsylvania Democrats managed to flip the State House in a "shocking upset", with a net gain of 12 seats giving them a bare 1-seat majority (due to two resignations and one death, however, Democrats weren't officially in the majority until February 2023). Democrats' majority, however, wouldn't have been possible without Conservative (but pro-labor) Democrat Frank Burns' victory in HD-72, located entirely within Cambria County. Burns has held onto this ancestrally Democratic seat since 2008, even as it is voted increasingly Republican federally and statewide (Josh Shapiro lost HD-72 by 7.5% even as he won by double digits statewide and Trump won the district by >40% in 2024). In 2022, Burns once again held his seat, defeating Republican Renae Billow by slightly less than 9% and giving Democrats control of the chamber. Following the election and Democrats' extremely thin majority, Burns was (and still is) a key figure in the State House. Burns narrowly won re-election in 2024, but how long his bipartisan appeal will last remains to be seen.