On June 5, 1999, at 0830 eastern daylight time, a homebuilt Pitts S-1S was substantially damaged after a loss of control during landing at the Freeway Airport (W00), Mitchellville, Maryland. The certificated airline transport pilot was not injured. Visual meteorological conditions prevailed and no flight plan was filed for the local flight conducted under 14 CFR Part 91. In a telephone interview, the pilot said he landed on runway 18 at Freeway. He said he applied the brakes and experienced no braking action on the left side. The airplane departed the right side of the runway, struck a ditch, nosed over, and came to rest inverted. The pilot, also a certificated airframe and powerplant mechanic, said he experienced problems with the left brake in the recent past, and had attempted to repair the problem on two separate occasions in the month prior to the accident. He said: "I'd had some trouble with my left brake. I changed the 'O' rings and cleaned the disks and pads. I then ground tested and flew the airplane. A flight or so later, I had the problem again, so I replaced the pads. On the third occurrence, I suffered the accident." The pilot said he contacted the brake manufacturer for information about the system, and to verify that the brake disks measured to the manufacturer's specifications. According to the pilot, "The brakes are needed to stop and to steer. It's a high priority thing, that's why I put so much effort into it." Examination of maintenance records revealed the pilot performed brake repairs on May 17, 1999, and again on June 4, 1999. The pilot reported that, other than the left brake, the airplane operated with no mechanical deficiencies. The pilot reported a total of 3,200 hours of flight experience on October 6, 1998. Federal Aviation Administration (FAA) Inspectors performed a cursory examination of the wreckage. In a telephone interview, an FAA Inspector stated that the left brake was not operational, and that the right brake did function. The airplane was inspected by an FAA Airworthiness Inspector on June 7, 1999. According to the Inspector, "The left brake caliper was broken at the forward dowel pin hole." The FAA Inspector conducted a telephone interview with the pilot. According to the Inspector's record of telephone conversation: "[The pilot] stated that, during conversations with other Pitts owners, he heard that this brake configuration was a known problem. He said that he was told that later models did not have the caliper installed on the bottom of the disk, as this one is. [The pilot] also stated that on more than one occasion he had the brake activate on bumpy runways. He was told it was due to the caliper location."