Vitali Klitschko (2003)

42-2, 39 KOs

Height: 6'7"

Weight: 250 lbs

Reach: 80'

Result:  Vitali TKO Round 10

Wladimir has better skills then his older brother, but Vitali's better chin and stamina would decide the fight. It would likely be a plodding fight with both men attempting to establish the jab.

Wladimir, with better speed, would be more effective early on. The fight changes when Wladimir catches a clean shot and goes down.

From then on, Vitali would press the action while Wladimir goes into a shell. The referee stops the fight after an exhausted Wladimir goes down in the 10th round. 

Lennox Lewis (2002)

41-2-1 32 KOs 

Height: 6'5"

Weight: 245 lbs

Reach: 84'

Result: Lewis KO in Round 9

Wladimir doesn't have the stamina or chin to go after Lewis like his brother did. Lewis would wear down and knockout Wladimir. It is likely that Lewis would be in some trouble early, but manage to survive.

He might hold a slight speed edge, but doesn't put punches together as well as Lewis. Since they are similar sizes, both men have to fight within each other's range. This really hurts Wladimir, as he has shown almost no ability to take a punch. 

Evander Holyfield (1991)

44-10-2 29 KOs

Height: 6'2"

Weight: 210 lbs

Reach 78'

Result: Unanimous decision for Klitschko

Holyfield struggles to get by the jab of Klitschko, and when he does get through, he is easily tied up by the much bigger man.

This also stops Holyfield from fighting at the quick pace he wants.

Holyfield wobbles Klitschko a few times, but is mostly on the receiving end of stiff jabs and is unable to mount an effective attack.   

Mike Tyson (1988)

50-6 44 KOs

Height: 5'10"

Weight: 218 lbs

Reach: 71'

Result: Tyson KO in Round 2

The speed, power and ferocity of a prime Mike Tyson stops Klitschko in the second round.

The first round is rather cautious, with Wladimir on the outside and Tyson patiently stalking. Tyson unloads late in the first round, with the bell saving Klitschko. The next round is the last as Klitschko is floored twice and fails to get up.

A flaw of Wladimir's is his predictable attack. Tyson figures this out early and takes advantage of it.

Larry Holmes (1980)

69-6  44 KOs

Height: 6'3"

Weight: 215 lbs

Reach: 81'

Result: Holmes by unanimous decision after 15 rounds

Holmes' quickness allows him to get the better of Wladimir.

It is mostly a battle of jabs, but Holmes is better able to throw combinations. Both men hit the canvas during the fight, but it doesn't alter the flow.  Klitschko wins a number of rounds, but Holmes is the clear winner.

Ken Norton (1976)

42-7-1 33 KOs

Height: 6'2"

Weight: 218 lbs

Reach: 80'

Result:  Klitschko KO in Round 2

Norton struggled against bigger men with power. He did well against boxers such as Holmes, but got blown out by George Foreman and Gerry Cooney.

Manny Steward advises Klitschko to press early and Norton wilts to the pressure.

George Foreman (1973)

76-5 68 KOs

Height: 6'3"

Weight: 225 lbs

Reach: 82'

Result: Klitschko KO in Round 5

This may seem like an odd result given Klitschko's bad chin, but Foreman was very sloppy back then and wasn't very fast.

Essentially he'd just try to bludgeon Klitschko with little regard to strategy. Wladimir is smart enough to survive a one-dimensional attack like that.

Once Foreman slowed down, he'd be ripe for straight rights from Klitschko. 

Joe Frazier (1971)

32-4-1, 27 KOs

Height: 5'11"

Weight 205 lbs

Reach: 73'

Result: Klitschko KO in Round 3

Joe Frazier's style simply will not work against a big man with power.

Klitschko is the worst possible matchup for Frazier. Watch both Frazier/Foreman fights to see how this one will go.

Muhammad Ali (1967)

56-5, 37 KOs

Height: 6'3"

Weight: 211 lbs

Reach: 82'

Result: Ali by TKO in Round14.

The fight is initially close, with the size and style of Klitschko troubling the dancing Ali. Klitschko's lack of variety on offense and predictability allow Ali to take control.

The referee stops it in the 14th as Klitschko is exhausted and unable to defend himself.

Wladimir Klitschko's style of boxing protects his two most vulnerable qualities: his chin and his stamina. He does this by keeping opponents outside using his jab, completely dictating the pace and style of the fight.

When he's able to pull this off, he's unbeatable.

Each fighter that I saw beating him was able to force Klitschko into a fight that exposed his chin and forced him to fight at a quicker pace. Except Tyson, every fighter that I picked to beat him was big, smart and had a good long jab.

Ali and Holmes were way too fast. Vitali and Lewis were too durable. Tyson in his prime had such a tremendous combination of speed power and ring smarts that he would have gotten an early shot in.

The losing fighters were all too small and liked to fight inside, except Foreman. I believe Foreman had the skills to beat Klitschko, but lacked the discipline. Frazier and Norton had disastrous results against big powerful boxers. Holyfield's problems with Lewis tell me he would struggle with Klitschko.