Under the guidance of Chris Hobbs, Fran Decker, and Dennis McNulty, the Timothy Christian boys basketball program has grown to tremendous heights since joining the Greater Middlesex Conference. However, the majority of the 20-win seasons at TCS occurred before that time.
Led by legendary head coach Bill Bills and his successor, Michael Carl, and players such as Mark Anselmo, Keith Christopher, and the Waszaj brothers (Jairo, Jason, Jon, and Tommy), the Tigers compiled four of their five 20-win campaigns over a seven-year stretch.
| Season | Wins | Losses | Win % |
| 2011-12 | 22 | 6 | 0.786 |
| 1999-2000 | 21 | 8 | 0.724 |
| 1998-99 | 21 | 10 | 0.677 |
| 2002-03 | 20 | 7 | 0.741 |
| 1997-98 | 27 | 5 | 0.786 |