#3 Bobby Lashley
Again, much like Dolph Ziggler, Bobby Lashley was making his name on SmackDown while The Undertaker was still a full-time star on the brand. However, the stars never aligned. Back in 2006, Lashley was being built as a powerhouse babyface while the Deadman was tasked with taking on some emerging heels like The Great Khali, MVP, and Mr. Kennedy.
However, the biggest tease for a match between The Undertaker and Lashley came after the latter left for ECW. The Deadman won the 2007 Royal Rumble Match and appeared on the following week's episodes of RAW, ECW, and SmackDown to scare the top Champion of every brand, John Cena, Batista, and Bobby Lashley.
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And while he picked The Animal, 'Taker would have had a great match with either Superstar. The Dominator was coming into his own as a performer, with The Deadman possibly helping him further.
Right now, a match between The Undertaker and Bobby Lashley would only be a possibility if he has more than a few matches left in the tank. If it does happen, it would be thanks to the strong position on the card Lashley has found himself in lately. He has recently taken up MVP as a manager and may win the WWE Championship at Backlash, along with a possible showdown with Brock Lesnar in the near future.