The 33rd International 500-Mile Sweepstakes was an automobile race held at the Indianapolis Motor Speedway on Monday, May 30, 1949.

After two years of failures to his teammate, Bill Holland finally won one for himself. Giving car owner Lou Moore his third consecutive Indy victory. Mauri Rose was fired by the team after the race when he again ignored orders and tried to pass Holland, only to see his car fail with 8 laps to go.^[3]

Spider Webb suffered a broken transmission the morning of the race and failed to start. Rather than utilize an alternate starter, officials awarded Webb the 33rd finishing position.

Offenhauser-powered cars locked 28 out of the 33 starting positions, and the top 19 finishing positions.

Row	Inside		Middle		Outside
1	54	Duke Nalon	5	Rex Mays	33	Jack McGrath
2	7	Bill Holland	17	Duane Carter	22	George Connor
3	61	Jimmy Jackson	26	George Lynch  R	98	Johnny Mantz
4	3	Mauri Rose  W	14	Hal Cole	12	Johnnie Parsons  R
5	2	Myron Fohr  R	8	Mack Hellings	29	Duke Dinsmore
6	77	Joie Chitwood	57	Jackie Holmes  R	64	Troy Ruttman  R
7	19	Paul Russo	6	Lee Wallard	68	Jim Rathmann  R
8	4	Bill Sheffler	18	Sam Hanks	71	Norm Houser  R
9	38	George Fonder  R	37	Spider Webb	10	Charles Van Acker
10	32	Johnny McDowell  R	69	Bayliss Levrett  R	74	Bill Cantrell
11	15	Fred Agabashian	9	Emil Andres	52	Manny Ayulo  R

• First alternate: Ralph Pratt  R  (#34)^[4]

Finish	Start	No	Name	Chassis	Engine	Qual	Rank	Laps	Status
1	4	7	Bill Holland	Diedt	Offenhauser	128.673	9	200	121.327 mph
2	12	12	Johnnie Parsons  R	Kurtis Kraft	Offenhauser	132.900	2	200	+3:11.00
3	6	22	George Connor	Lesovsky	Offenhauser	128.228	13	200	+3:34.81
4	13	2	Myron Fohr  R	Marchese	Offenhauser	129.776	3	200	+5:16.68
5	16	77	Joie Chitwood	Kurtis Kraft	Offenhauser	126.863	27	200	+5:21.00
6	7	61	Jimmy Jackson	Diedt	Offenhauser	128.023	15	200	+7:15.03
7	9	98	Johnny Mantz	Kurtis Kraft	Offenhauser	127.786	18	200	+8:50.04
8	19	19	Paul Russo	Slines	Offenhauser	129.487	5	200	+20:55.31
9	32	9	Emil Andres (Walt Brown Laps 19–197)	Slines	Offenhauser	126.042	31	197	Flagged
10	24	71	Norm Houser  R	Langley	Offenhauser	127.756	20	181	Flagged
11	21	68	Jim Rathmann  R	Wetteroth	Offenhauser	126.516	29	175	Flagged
12	18	64	Troy Ruttman  R	Wetteroth	Offenhauser	125.945	32	151	Flagged
13	10	3	Mauri Rose  W	Diedt	Offenhauser	127.759	19	192	Magneto strap
14	5	17	Duane Carter	Stevens	Offenhauser	128.233	12	182	Spun T3
15	15	29	Duke Dinsmore	Olson	Offenhauser	127.750	21	174	Radius rod
16	14	8	Mack Hellings	Kurtis Kraft	Offenhauser	128.260	11	172	Valve
17	22	4	Bill Sheffler	Bromme	Offenhauser	128.521	10	160	Rod
18	28	32	Johnny McDowell  R	Meyer	Offenhauser	126.139	30	142	Magneto
19	11	14	Hal Cole	Kurtis Kraft	Offenhauser	127.168	24	117	Rod bearing
20	25	38	George Fonder  R  (Mel Hansen Laps 68–116)	Adams	Sparks	127.289	22	116	Valve
21	30	74	Bill Cantrell	Kurtis Kraft	Offenhauser	127.191	23	95	Drive shaft
22	17	57	Jackie Holmes  R	Kurtis Kraft	Offenhauser	128.087	14	65	Drive shaft
23	20	6	Lee Wallard	Maserati	Maserati	128.912	7	55	Gears
24	29	69	Bayliss Levrett  R	Kurtis Kraft	Offenhauser	129.236	6	52	Drain plug
25	2	5	Rex Mays	Kurtis Kraft	Novi	129.552	4	48	Engine
26	3	33	Jack McGrath	Kurtis Kraft	Offenhauser	128.884	8	39	Oil pump
27	31	15	Fred Agabashian	Maserati	Maserati	127.007	25	38	Overheating
28	33	52	Manny Ayulo  R	Bromme	Offenhauser	125.799	33	24	Rod
29	1	54	Duke Nalon	Kurtis Kraft	Novi	132.939	1	23	Crash T3
30	23	18	Sam Hanks	Kurtis Kraft	Offenhauser	127.809	17	20	Oil leak
31	27	10	Charles Van Acker	Stevens	Offenhauser	126.524	28	10	Crash T4
32	8	26	George Lynch  R	Rassey	Offenhauser	127.823	16	1	Crash T1
33	26	37	Spider Webb	Bromme	Offenhauser	127.002	26	0	Transmission
[6][7]

Note: Relief drivers in parentheses^[8]

 W  Former Indianapolis 500 winner

 R  Indianapolis 500 Rookie

All entrants utilized Firestone tires.

The race was carried live on the Mutual Broadcasting System, the precursor to the IMS Radio Network. The broadcast was sponsored by Perfect Circle Piston Rings and Bill Slater served as the anchor. The broadcast featured live coverage of the start, the finish, and live updates throughout the race.

The race was carried live for the first time in the history of television on WFBM-TV Channel 6 of Indianapolis. The station signed on for the first time on the morning of May 30, 1949,^[11] with a documentary about the race entitled The Crucible of Speed, then coverage of the race itself. The race broadcast used three cameras located along the front stretch. Earl Townsend, Jr. who previously worked as a radio reporter, was the first television announcer. Dick Pittenger and Paul Roberts joined Townsend along with engineer Robert Robbins. The telecast reached approximately 3,000 local households.

• 1949 AAA Championship Car season

• 1949 Indianapolis 500 Radio Broadcast, Mutual: Re-broadcast on "The All-Night Race Party" – WIBC-AM (May 28, 2005)
• Van Camp's Pork & Beans Presents: Great Moments From the Indy 500 – Fleetwood Sounds, 1975