Tony Kanaan had another terrible Indy 500 when he crashed before the halfway mark and finished 27th in a 33-car field. If the past is any indication though, he should rebound nicely this week. The Indy Racing League has been going to the Milwaukee Mile for five years and Kanaan has never finished outside the top-five there. In fact, he took top honors in back-to-back season in 2006 and 2007, which makes him one of the favorites to win again this week.
Nearly as stout, Dario Franchitti is back from his NASCAR sojourn and he's never finished worse than sixth in four starts on this track. He won the inaugural race in 2004 and then posted runner-up results in 2005 and 2007. Last week, he was in contention for the 500 victory until trouble in the pits relegated him to seventh, so he will be looking for redemption.
Dan Wheldon does not have the overall numbers of Kanaan and Franchitti, but he's certainly come on strong lately. He struggled to an 18th-place finish in 2004 and was a modest eighth in 2006, but every other result has been a top-five—and that is enough to recommend him for this week's Milwaukee race.
Results, Last five years
| Driver | Avg Finish | 2008 | 2007 | 2006 | 2005 | 2004 |
| Tony Kanaan | 2.60 | 3 | 1 | 1 | 4 | 4 |
| Dario Franchitti | 2.75 |
| 2 | 6 | 2 | 1 |
| Sam Hornish Jr | 3.75 |
| 9 | 2 | 1 | 3 |
| Oriol Servia | 6.00 | 6 |
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| Justin Wilson | 7.00 | 7 |
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| Patrick Carpentier | 7.00 |
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| 7 |
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| Bryan Herta | 7.33 |
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| 7 | 6 | 9 |
| Alex Barron | 7.50 |
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| 8 | 7 |
| Dan Wheldon | 7.60 | 4 | 3 | 8 | 5 | 18 |
| E J Viso | 8.00 | 8 |
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| Adrian Fernandez | 8.00 |
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| 8 |
| Townsend Bell | 8.50 | 11 |
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| 6 |
| Jeff Simmons | 9.50 |
| 10 | 9 |
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| Danica Patrick | 10.00 | 9 | 8 | 4 | 19 |
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| Scott Dixon | 10.20 | 2 | 4 | 10 | 13 | 22 |
| Scott Sharp | 10.75 |
| 6 | 12 | 10 | 15 |
| Tomas Scheckter | 11.00 |
| 17 | 3 | 3 | 21 |
| Vitor Meira | 11.20 | 22 | 5 | 15 | 9 | 5 |
| Buddy Rice | 11.60 | 10 | 18 | 11 | 17 | 2 |
| Hideki Mutoh | 12.00 | 12 |
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| Kosuke Matsuura | 12.50 |
| 12 | 17 | 11 | 10 |
| Helio Castroneves | 12.60 | 5 | 16 | 14 | 16 | 12 |
| Felipe Giaffone | 13.00 |
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| 13 |
| Jeff Bucknam | 13.00 |
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| 13 |
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| Ed Carpenter | 13.20 | 20 | 7 | 16 | 12 | 11 |
| Ryan Briscoe | 13.67 | 1 |
| 18 | 22 |
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| Marco Andretti | 13.67 | 21 | 15 | 5 |
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| Mark Taylor | 14.00 |
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| 14 |
| Jimmy Kite | 14.00 |
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| 14 |
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| Will Power | 14.00 | 14 |
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| Sarah Fisher | 14.00 |
| 14 |
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| Anthony Foyt IV | 16.75 | 17 | 13 |
| 21 | 16 |
| Roger Yasukawa | 15.00 |
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| 15 |
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| Ryan Hunter-Reay | 15.00 | 15 |
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| Darren Manning | 15.75 | 13 | 11 |
| 20 | 19 |
| Enrique Bernoldi | 16.00 | 16 |
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| Jaques Lazier | 17.00 |
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| 17 |
| Bruno Junqueira | 18.00 | 18 |
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| Buddy Lazier | 18.00 |
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| 18 |
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| A J Foyt IV | 16.75 | 17 | 13 |
| 21 | 16 |
| John Andretti | 19.00 | 19 |
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| Tora Takagi | 20.00 |
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| 20 |
| Mario Moraes | 23.00 | 23 |
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| Jaime Camara | 24.00 | 24 |
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| Graham Rahal | 25.00 | 25 |
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| Mario Dominguez | 26.00 | 26 |
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| Marty Roth | 27.00 | 27 |
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