Trojans
Address: 180 Church St., Ajax, L1T 2W7 (map)
School opened: 1951
Enrollment / OFSAA classification: 1309 / AAAA
Pickering High School Sports Web Site
Senior Program
LOSSA Football Membership: 2003-present; 1973-2001; 1970-71
Titles: Thirteen (2006, 2005, 2004, 1994, 1993, 1990, 1989, 1988, 1986, 1983, 1981, 1976, 1975)
2008 Players to watch:
Daniel Heslop
Junior Program
LOSSA Football Membership: 2002-present; 1976-97; 1973; 1970-71
Titles: Eight (2002, 1997, 1995, 1994, 1990, 1989, 1981, 1980)
2008 Players to watch:
Taylor Eskins
Where Are They Now!
| Player | University / College | Current Team |
| Aiello; Frank | Attending Bishops University | Bishop Gaiters (DL) |
| Brooks; Tim | Attending Bishops University | Bishops Gaiters (LB) |
| Brown; Adam | Attending University of Windsor | Windsor Lancers (DB) |
| Elliott; Broc | Attending York University | York Lions (LB) |
| Exeter; Lance | Attending Ryerson University | Retired |
| Greene; Andrew | Attended Indiana University (U.S.) | Saskatchewan Roughriders (CFL: OG) |
| Herbert; Shane | Attending Wilfrid Laurier University | Wilfrid Laurier Golden Hawks (CB) |
| Lock; Dylan | Attending University of Western Ontario | Western Mustangs (Injured) |
Noteworthy:
1981: The senior Trojans join the Henry Street Hawks as three time senior champions as they defeat the Paul Dwyer Saints 20-6. The junior Trojans capture the league title with a 40-14 romp over the Paul Dwyer Saints becoming the first school in LOSSA junior football history to successfully defend their title. The combined junior/senior championship duplicates the feat accomplished by Henry Street in 1979.
1980: Returning to the championship final for the first time in seven years, the junior Trojans shut out the Eastdale Eagles 10-0 to earn their first LOSSA junior football title.
1977: Pickering's quest for three consecutive senior championships is thwarted by the Henry Street Hawks, who hand the Trojans a 19-6 setup in the league finals.
1976: The Senior Trojans become the first football program to repeat as LOSSA champions prevailing by a 7-0 score over the Eastdale Eagles. The back to back shut outs by Pickering in the senior Championship finals has never been duplicated,
1975: The Pickering Senior team routs the Anderson Raiders 43-0 to gain their first LOSSA senior championship. The 43 point margin of victory remains the largest margin in a championship senior final.
1973: The Junior Trojans advance to the LOSSA championship against the Uxbridge Tigers. At the end of regulation time, the two teams were tied. Uxbridge would prevail in overtime by a score of 21-15.
1960: The Pickering Trojans, stocked with inexperienced players, are thoroughly defeated 99-6 by Oshawa Central. Trojan football would go to the back burner for nearly a decade.