» May 10, 1996:
The Red Sox edge the Blue Jays, 6–5, in 11 innings. John Valentin ties the score with a 2-out homer in the 9th and Troy O'Leary homers in the 11th to win it. Heathcliff Slocumb, Tom Gordon, and Mike Stanton combine to strike out 17 Jays. » April 29, 1997:
At Boston, CF Shane Mack is the only outfielder not to throw out a runner. All three California outfielders -- Tim Salmon, Garret Anderson and Orlando Palmeiro -- do it, while Red Sox starting LF Wil Cordero and Troy O'Leary, who replaced Rudy Pemberton in RF, register one. The Angels win the contest by a score of 5–4. Tomorrow, Anderson and Cordero will throw out runners again.
» August 5, 1997: The Red Sox pound out 24 hits, including four home runs, in defeating the Rangers, 17-1. Nomar Garciaparra is 4-for-7 with a homer and two doubles and Troy O'Leary homers twice into the upper deck.
» October 11, 1999: The Red Sox defeat the Indians, 12-8, to win their league division series, 3-games-to-2. Troy O'Leary's two home runs, including a grand slam, power the Sox to the victory, as the OF drives home seven of Boston's runs. Nomar Garciaparra draws two intentional walks and both times O'Leary follows with a Pedro Martinez picks up the win by hurling six hitless innings in relief for the Sox.
» May 9, 2001: Red Sox 2B Chris Stynes, who had three hits in yesterday's win, suffers two fractures in his left cheekbone when he is hit by an Aaron Sele pitch in the 2nd inning. He'll miss six weeks. Seattle breaks a 5–5 tie in the 8th on John Olerud's double to win, 10–5. David Bell has four RBI for the M's, while Trot Nixon homers and Manny Ramirez and Troy O'Leary go back-to-back in the 4th.
» December 17, 2002:
The Cubs sign free agent OF Troy O'Leary to a one-year contract for $750,000.