On August 21, 2001 — 2001 – The International League’s Triple-A game between Rochester (Orioles) and Ottawa (Expos) features Tim Raines and his son Tim Jr. as opponents. It is believed to be the first contest involving a dad and his son facing each other during the regular season on the professional level. The two will briefly be teammates with the Orioles at the end of the season.
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Sources:
Baseball Reference August 21
National Pastime August 20
Retro Sheet
Hall of Fame
SABR Games Project
Replay The Game