About Us

The Chapel Hill Wiffleball League is open to anyone and everyone. Founded by Chapel Hill legend Sean Oglesby, the league has grown in each of its ten year existence and it continues to. The annual World Series is open to anyone to enter and is a blast for all ages. This is not traditional wiffleball though, Chapel Hill Wiffleball is a unique mix between traditional baseball and wiffleball and is very physically demanding and action packed. The Chapel Hill Wiffleball league was founded in the year 2000. The league began at historic Chapel Hill Field adjacent to the Chapel Hill swim club in the North Hills of Pittsburgh. The league began with pick up play but has evolved into an organization that hosts the annual Wiffleball World Series. The series began in 2005 and is the event of the summer for hundreds of kids throughout the Pittsburgh area.


This story is for everybody who has played Chapel Hill wiff, participated in one of our amazingly organized tournaments, or is a die hard CHWL fanatic like the 5 founding fathers. Myself, Bebo, Bob Ralls, Dave Bay or Roges... Chapel Hill Field is located off Browns Lane behind Northway Mall next to the Chapel Hill Swim Club. People have been playing there for as long as I can remember, and probably before i was born. But Chapel Hill Wiffleball really took off in about 2000 when some new pool opened and alot of the older North Hills kids left Chapel Hill and relocated there. At this time the crew (me, Brandon Jackson, Ryan Oglesby, and David Bailey) all became friends and sort of took over the field. Bob Ralls came into the picture a year later and was really bad at wiffleball... but he has made tremendous steps and has become an all star. As the years went on the stakes grew higher. As many of you may remember, one of the greatest events in Chapel Hill history was the Pa Palooka Mid-Summer Classic which occured in the summer of 2005(AKA the first annual Chapel Hill wiffleball world series). It was an 8 team money tournament played not only at Chapel Hill but also across the street at Northway Elementary. This tournament was a scandal! The Kekambas player and umpire of the pool A Championship game, David Dunton blew crucial calls for the Pa Palooka against the underdog Chapel Hill Bombers, just to get the game over with more quickly. One of these calls was an out call against Matt Robertson at first base in which he was clearly safe and beat the throw by a few steps... The Bombers led by Chapel Hill great Ryan Oglesby went on to beat the #1 ranked Pa Palooka (who competed in an invitational downtown that same summer) and went on to the tournament championship to face Dave Dunton and his Kekambas. Dave’s calls came back to bite him in the ass... as the Chapel Hill Bombers who were a huge underdog and were also 2 years younger than almost every Kekamba player routed them for a win of almost 20!! The League has gone on to have many successful money tournaments and is still strong today. The Chapel Hill Wiffleball league has grown along with its players and unfortunately they have outgrown the confines of historic Chapel Hill Park. The memories and traditions will live on there, but as for The Chapel Hill Wiffleball League today, we had our inaugural tournament at Espe Park in 2009 and it proved to be worthy enough to be called the new home of this great league.