#3 Triple H vs Randy Orton (Wrestlemania 25 - April 5, 2009)
Considering the immense talent of Triple H and Randy Orton, their lack of chemistry in the ring is extraordinary.
After having contested dismal bouts in 2004, 2007 and 2008, WWE strangely decided to book them in the main event of it's heavily hyped Wrestlemania 25 show.
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Considering the original plan was for the Wrestlemania Championship matches to pit Triple H versus John Cena and Randy Orton versus Edge, which then were fresh matches, it is even more baffling that the company decided to change course.
The only legitimately great match of their run together was a Last Man Standing Match at No Mercy 2007 but despite stipulations being imperative to making a match between the pair worthwhile, the Wrestlemania encounter had none.
Making matters worse, Triple H versus Orton followed the instant classic five-star encounter between Shawn Michaels and The Undertaker.
Part of the problem was that Triple H and Orton had battered each other in a long series of over the top angles such as Orton RKO'ing Triple H's wife Stephanie and "The Game" invading and destroying Orton's house with a sledgehammer.
By the time, Wrestlemania rolled around there was nothing they had not done to each other and without a stipulation was a major anti-climax.
For 25 deathly dull minutes, the pair traded rest holds and repetitive slams while the crowd sat on its hands.
The worst Wrestlemania main event of all time.