87th Grey Cup The 87th Grey Cup ( Canadian Football League championship ) was held in 1999 in Vancouver . The Hamilton Tiger - Cats won the game 32 - 21 over the Calgary Stampeders in a rematch of the previous year ' s 86th Grey Cup . Game summary . Hamilton Tiger - Cats ( 32 ) - TD ' s , Ronald Williams , Darren Flutie ( 2 ) ; FG ' s , Paul Osbaldiston ( 3 ) ; cons . , Osbaldiston ( 3 ) ; singles , Osbaldiston ( 2 ) . Calgary Stampeders ( 21 ) - TD ' s , Vince Danielson , Allen Pitts , Duane Forde ; cons . , Mark McLoughlin ( 3 ) . First Quarter < br > HAM — TD Williams 1 yard run ( Osbaldistan convert ) 4 : 52 < br > HAM — FG Osbaldiston 46 yard field - goal 13 : 39 < br > Second Quarter < br > HAM — Single Osbaldiston missed 56 yard field - goal attempt , one - point granted 0 : 44 < br > HAM — FG Osbaldiston 41 yard field - goal 9 : 26 < br > HAM — TD Flutie 13 yard pass from McManus ( Osbaldiston convert ) 13 : 57 < br > Third Quarter < br > HAM — Single Osbaldiston missed 41 yard - field goal attempt , one - point granted 1 : 34 < br > CAL — TD Danielson 7 yard pass from Dickenson ( McLoughlin convert ) 4 : 55 < br > CAL — TD Pitts 18 yard pass from Dickenson ( McLoughlin convert ) 9 : 57 < br > HAM — FG Osbaldiston 20 yard field - goal 13 : 08 < br > Fourth Quarter < br > HAM — TD Flutie 7 yard pass from McManus ( Osbaldiston convert ) 0 : 39 < br > CAL — TD Forde 1 yard run ( McLoughlin convert ) 12 : 00 The Tiger - Cat started off strong from the opening kick - off . Midway through the first quarter , the Tiger - Cats got on the board as McManus hit Williams for a 35 - yard gain to the Stamps ' 15 - yard line . Three plays later , Williams plunged into the end zone from one - yard out to give the Tiger - Cats a 7 - 0 lead . On Hamilton ' s next possession , McManus found Flutie for a 40 - yard gain as the Tiger - Cats again moved into Calgary territory . That led to a 46 - yard field goal from Paul Osbaldiston to give the Tiger - Cats a 10 - 0 advantage , as the gun sounded to end the first quarter . With almost four minutes gone in the second quarter , the Stampeders finally picked up their first first down when Kelvin Anderson ran wide near midfield . However they were unable to sustain the drive . Midway through the second quarter , the Hamilton offence drove downfield as McManus passed to Darren Flutie and Andrew Grigg culminating in a 41 - yard field goal by Osbaldiston . Late in the half , Calgary punter Tony Martino pinned the Tiger - Cats deep with a 42 - yard punt that went out of bounds at the 4 - yard line . The move appeared to pay off but the Hamilton defence then took centre stage . When Joe Montford sacked Calgary quarterback Dave Dickenson , the ball came loose and Tim Terry scooped it up . From there , McManus found Flutie open in the end zone and he made a one - hand grab for the touchdown . The Stamps had only 51 yards in total offence in the first half . The Stamps tried some trickery on the second half kickoff with an onside kick but the Tiger - Cats recovered the ball with good field position . Osbaldiston turned that into a single point . Then came the biggest play of the game for Calgary . Dickenson spotted Travis Moore behind the Hamilton defence and completed a 57 - yard pass down to the 7 - yard line . On the next play , Dickenson passed to Danielsen , who took it in for the touchdown to put the Stamps on the board . On their next possession , the Stampeders took the ball down the field again and Dickenson found Pitts wide open in the end zone to close the gap to 22 - 14 . Osbaldiston added a 20 - yard field goal late in the quarter to take some momentum away from the resurgent Stampeders . McManus then engineered a drive to open the fourth quarter culminating in a touchdown pass to Flutie . Calgary ' s next possession was ended by an interception by Orlondo Steinauer . Calgary regained possession , Dickenson drove deep into Hamilton territory and , on third down , Duane Forde plunged over the goal line with just over three minutes remaining . The Stamps were unable to score again and so came up short as the Tiger - Cats won 32 - 21 . Notable facts . Grey Cup Most Valuable Player Danny McManus led the way connecting on 22 of 34 passes for 347 yards and no interceptions . Darren Flutie was also impressive , pulling in six catches for 109 yards and two touchdowns . Cats kicker Paul Osbaldiston chipped in with three field goals , while slotback Mike Morreale caught three passes for 51 yards and was named the game ' s Most Valuable Canadian .