| Date | Opponent | Result | Recap |
|---|
| Preseason |
| October |
| 2008-10-07 | @CLE | W 104-85 | Lebron plays 8 minutes. Full Recap |
| 2008-10-08 | NYK | W 113-111 | No defense against suprirsingly motivated Knicks. Full Recap |
| 2008-10-12 | PHI | L 79-85 | Iggy drives on Kapono for a dunk to seal tight game. Full Recap |
| 2008-10-14 | MOS | W 86-78 | Bosh comes up big as embarassment saved. Full Recap |
| 2008-10-16 | MIN | L 86-90 | Rocked by T’Wolves’ athleticism. Full Recap |
| 2008-10-18 | @LAC | W 93-89 | Bosh, O’Neal with perfect games. Full Recap |
| 2008-10-19 | @LAL | L 89-112 | Good three quarters. Terrible 4th quarter. Full Recap |
| 2008-10-21 | DEN | L 94-105 | Aggressive Denver attacks the rim all night long. Full Recap |
| Regular Season |
| 2008-10-29 | @PHI | W 95-84 | Bosh, O’Neal man the paint and keep Philly on the perimeter. Full Recap |
| 2008-10-31 | GSW | W 112-108 | Bosh comes through in the clutch. Full Recap |
| November |
| 2008-11-01 | @MIL | W 91-87 | The seven man rotation strikes again as big Jose 3 decides affair. Full Recap |
| 2008-11-05 | DET | L 93-100 | Nobody could guard Tayshaun Prince. Nobody. Full Recap |
| 2008-11-07 | @ATL | L 92-110 | Moon and Parker pwn3d by Atlanta SFs. Full Recap |
| 2008-11-09 | @CHA | W 89-79 | Helped by Bargnani, Bosh takes over in the fourth. Full Recap |
| 2008-11-10 | @BOS | L 87-94 | Pierce takes over in 4th. Bosh doesn’t show up. Full Recap |
| 2008-11-12 | PHI | L 96-106 | Wings go 6/28 and waste Big 3 effort. Philly too athletic. Full Recap |
| 2008-11-16 | MIA | W 107-96 | Bargnani start sparks win. Full Recap |
| 2008-11-18 | @ORL | L 90-103 | Will Solomon gets the start. Full Recap |
| 2008-11-19 | @MIA | W 101-95 | Bosh, O’Neal and Bargnani with big games. Full Recap |
| 2008-11-21 | NJN | L 127-129 | VC takes over as Mitchell fails us yet again. Full Recap |
| 2008-11-23 | BOS | L 103-118 | Rondo schools Calderon. Raptors don’t give any effort. Full Recap |
| 2008-11-26 | CHA | W 93-86 | All Bosh and some Good Joey Full Recap |
| 2008-11-28 | ATL | W 93-88 | Bosh should wear a saddle. Good Joey again. Full Recap |
| 2008-11-30 | @LAL | L 99-112 | Rebounds 54-36, fastbreak points 18-7, PINP 58-32 and second-chance points 30-10. Bosh no-show. Full Recap |
| December |
| 2008-12-02 | @DEN | L 93-132 | No effort. An embarassment for the franchise. Full Recap |
| 2008-12-05 | @UTA | L 87-114 | Utah too efficient Full Recap |
| 2008-12-07 | POR | L 97-98 | It’s tough to overcome -17 rebounding and your superstar getting outplayed Full Recap |
| 2008-12-09 | @CLE | L 94-114 | Bad 1Q and 3Q start seals our fate. Bosh takes a nap. Full Recap |
| 2008-12-10 | IND | W 101-88 | Defense picks up, Indiana shoots 35%. Full Recap |
| 2008-12-12 | @NJN | W 101-79 | Best defensive performance of the year. Full Recap |
| 2008-12-14 | NOH | L 91-99 | David West outplays Chris Bosh. Too much Chris Paul. Full Recap |
| 2008-12-15 | NJN | L 87-94 | -16 total rebounds, -11 offensive rebounds and -24 second chance points. Full Recap |
| 2008-12-17 | DAL | L 86-96 | Dirk shows up, Bosh doesn’t. Full Recap |
| 2008-12-19 | @OKC | L 83-91 | No perimeter or transition defense. O’Neal leaves game. Full Recap |
| 2008-12-20 | @SAS | L 97-107 | Spurs drive ‘n kick for three all night long. Full Recap |
| 2008-12-22 | @LAC | W 97-75 | Bosh, O’Neal with big games as Camby and Kaman out with injury. Full Recap |
| 2008-12-26 | @SAC | W 107-101 | O’Neal with a monster game. Full Recap |
| 2008-12-27 | @POR | L 89-102 | No D for Brandon Roy in the fourth. Full Recap |
| 2008-12-29 | @GSW | L 111-117 | More fourth qurater choking. Kapono, Parker and Calderon miss open thres late on. Full Recap |
| 2008-12-31 | DEN | L 107-114 | No perimeter defense, 50 Denver PINP and an ill-advised Bosh three. Full Recap |
| January |
| 2009-01-02 | HOU | W 94-73 | Bargnani shows up again. T-Mac checks out. Full Recap |
| 2009-01-03 | ORL | W 108-102 | Roko Ukic. Roko Ukic. Roko Ukic. Full Recap |
| 2009-01-05 | @MIL | L 97-107 | Ukic benched for no reason late in fourth. Moon’s defense is laughable. Full Recap |
| 2009-01-07 | @WAS | W 99-93 | 9 Raptors down East’s worst team. Full Recap |
| 2009-01-09 | MEM | W 103-82 | Bosh abuses two rookies. Full Recap |
| 2009-01-11 | BOS | L 88-94 | Ray Allen hits 8 threes. Chris Bosh chokes against Kevin Garnett. Again Full Recap |
| 2009-01-12 | @BOS | L 109-115 | Raptors fail to score for 9 straight fourth quarter possessions. Full Recap |
| 2009-01-14 | CHI | L 98-102 | Noah blocks Bosh fadeaway late. Rose with 17 in fourth. Full Recap |
| 2009-01-16 | @IND | L 104-111 | Can’t wait till the 4th quarter to play hard. Full Recap |
| 2009-01-18 | PHO | L 113-117 | Parker impressive at PG but Raps fall short. Full Recap |
| 2009-01-19 | @ATL | L 84-87 | Jumpshotio Moon kills Raptors with worst shot of season. Full Recap |
| 2009-01-21 | @DET | L 76-95 | Nathan Jawai finally played. Full Recap |
| 2009-01-23 | @CHI | W 114-94 | Jose return sparks Raps. Full Recap |
| 2009-01-25 | SAC | W 113-97 | Lowly Kings come to town. Good game by Jose and Bosh. Full Recap |
| 2009-01-28 | @NJN | W 107-106 | Nets go on a 16-5 run to end game making this feel like a L. Full Recap |
| 2009-01-30 | MIL | L 85-96 | All jumpers in the third quarter. Bosh with 7 turnovers. Full Recap |
| February |
| 2009-02-01 | ORL | L 90-113 | Zero effort, Bosh checks out early. Full Recap |
| 2009-02-03 | @CLE | L 83-101 | LBJ explodes in first quarter, Raps rally but Cavs up D in 4th. Full Recap |
| 2009-02-04 | LAL | L 107-115 | Great effort but Kobe’s too clutch. Full Recap |
| 2009-02-06 | @NOH | L 92-101 | Hornets end on big run Full Recap |
| 2009-02-07 | @MEM | L 70-78 | More humiliation. Full Recap |
| 2009-02-10 | @MIN | W 110-102 | Joey Graham sparks Raps, Parker ups D in fourth. Full Recap |
| 2009-02-11 | SAS | W 91-89 | Roko in the clutch. Full Recap |
| 2009-02-18 | CLE | L 76-93 | Raps shoot 36.5%. Cavs shoot 58.0%. Full Recap |
| 2009-02-20 | @NYK | L 97-127 | Massacre at MSG. Full Recap |
| 2009-02-22 | NYK | W 111-100 | Bargnani pulls Raptors through. Full Recap |
| 2009-02-24 | MIN | W 118-110 | Bargnani once again, Raptors own Minny. Parker with a good game. Full Recap |
| 2009-02-27 | @PHO | L 113-133 | Shaq with 45, Suns with 90 points in the paint. Full Recap |
| March |
| 2009-03-01 | @DAL | L 98-109 | Jumper happy in the third – overall 37% shooting. Full Recap |
| 2009-03-03 | @HOU | L 97-107 | One too many offensive droughts and Louis Scola. Full Recap |
| 2009-03-06 | MIA | L 102-108 | Wade explodes. Full Recap |
| 2009-03-08 | UTA | L 101-109 | Bosh freezes down the stretch, Deron Williams doesn’t. Full Recap |
| 2009-03-11 | @PHI | L 106-115 | Terrible second quarter. A flu-ridden Bargnani was the only positive. Full Recap |
| 2009-03-13 | DET | L 95-99 | Bad start to overtime. At least the effort was there. Full Recap |
| 2009-03-15 | IND | W 110-87 | Bargnani comes up big. Jose’s second straight good game. Full Recap |
| 2009-03-16 | @CHA | L 86-112 | Lay down and die. Full Recap |
| 2009-03-20 | CHA | L 89-102 | Gerald Wallace with his best game. Ever. Full Recap |
| 2009-03-22 | LAC | W 100-76 | It’s the Clippers. Full Recap |
| 2009-03-25 | MIL | W 115-106 | Bucks disappoint, Jose and Bargnani go off. Full Recap |
| 2009-03-27 | OKC | W 112-96 | Young Thunder owned by Raptors. Full Recap |
| 2009-03-29 | CHI | W 134-129 | Bosh, Bargnani, Calderon, all except Parker come through. Full Recap |
| April |
| 2009-04-01 | @ORL | W 99-95 | Best win of the season. Bosh hits 22 footer to ice it. Full Recap |
| 2009-04-04 | @NYK | W 102-95 | Knicks held to 2 fastbreak points. Bargnani impressive. Full Recap |
| 2009-04-05 | NYK | L 103-112 | Zero defensive effort. Knicks drain a gazillion threes. Full Recap |
| 2009-04-07 | ATL | L 110-118 | At some point you’ll have to play some defense. Full Recap |
| 2009-04-08 | @IND | L 101-130 | Disgusting. Full Recap |
| 2009-04-10 | WAS | L 98-100 | Second half defense nowhere to be found. Butler breaks Marion at buzzer. Full Recap |
| 2009-04-12 | PHI | W 111-104 | Meh. Full Recap |
| 2009-04-13 | @WAS | W 97-96 | Hot-shooting Jamison injured in fourth. Bosh with a late three. Full Recap |
| 2009-04-15 | @CHI | W 109-98 | It all comes togehter. In the last game of the season. Full Recap |
