Alright, so I got thinking about the Boston Red Sox the other day, specifically about pitchers. You know, the real workhorses, the ones who could rack up wins. It popped into my head: who actually managed to win 20 games in a single season for the Sox? It sounds simple, but I figured it’d be interesting to actually track down the list.

So, first thing I did was just hop online. Typed something basic like “Red Sox pitchers 20 wins season” into the search bar. Man, that first wave of results was kind of all over the place. Lots of articles talking about recent pitchers, Cy Young awards, general team history. Not quite the straightforward list I wanted.
I realized I needed to get more specific. I remembered those hardcore baseball stats websites, the ones that have records going way, way back. Found one that looked promising, seemed to have tons of historical data.
Digging Into the Numbers
Okay, this site was better. But now I had to figure out how to navigate it. I looked for sections on team stats or player stats by season. Found a way to filter by team – selected Boston Red Sox, obviously. Then, I needed to find pitching stats specifically.
Once I got to the pitching leaderboards section, I looked for season stats. The trick was filtering it right. I needed:
- Individual pitcher seasons
- Filtered for the Red Sox
- And the key stat: Wins (W) >= 20
It took a bit of clicking around. Had to set the parameters just right. I sorted the seasons to see who popped up with 20 or more wins.
Compiling the Actual List
Slowly but surely, the names started showing up. I started jotting them down as I scrolled through the different eras. You see the expected legends pretty quick. Guys like Cy Young himself, way back when. Then you got Smoky Joe Wood. Moving forward in time, names like Lefty Grove and Wes Ferrell appeared.

It was cool seeing the more modern guys too. Roger Clemens did it multiple times, no surprise there. And of course, Pedro Martinez – watching him pitch was something else, seeing his name on the list felt right. Even Derek Lowe had one of those seasons. Rick Porcello was the most recent one I could find.
It wasn’t super complicated once I found the right place to look, but it did take a little focused effort to filter out the noise and get just that specific list. Pretty interesting to see how rare it actually is, especially in today’s game. Makes you appreciate those seasons even more.