Triple H has been with WWE for over two decades now, and he's taken down a long list of all-time greats. This includes The Undertaker, 'Stone Cold' Steve Austin, Kurt Angle, Hulk Hogan, John Cena, Shawn Michaels, and The Rock, among many others.
But there are some WWE legends—as well as some active veteran superstars—that have yet to lose to The Cerebral Assassin. Some of these guys are retired, but there are a handful of big-name talents that Triple H can still try to conquer for the first time.
After spending a brief time with WWE from 1999 to 2002, R-Truth left and joined the rival TNA promotion. He returned to WWE in 2008 and has stayed here ever since, working as a humorous mid-card performer.
R-Truth and Triple H have never squared off one-on-one before, but they were involved in the same tag team match at Vengeance 2011. Truth and The Miz (Awesome Truth), and they took down The Game and CM Punk in a tag team match. R-Truth has spent around 15 years total in WWE, yet he hasn't lost a single match to Triple H. Be sure to tell your friends!
9 Curtis Axel
Axel joined the WWE main roster in 2013 and went up against Triple H on the May 20 episode of Raw. That match ended in a no contest, with Triple H suffering a concussion that caused him to collapse during the fight.
The Game got his rematch three weeks later, but Vince McMahon came out and proclaimed a loss for Triple H via DQ. The latter wouldn't have any of it and was able to order a rematch right then in there. Once again, Vince called a default loss for Triple H. With that, The Game is 0-3 all-time against Axel, still awaiting his first win against the former Intercontinental Champion.
8 Kofi Kingston
The current WWE Champion debuted on the main roster 11 years ago, and he hasn't looked back. Kingston has been with WWE for over a decade now, and yet he and Triple H haven't crossed paths in any one-on-one or tag team matches.
You'd think that the two would have wrestled at least once by now, but no, sir. With Kingston in the midst of a massive main event run, one would have expected Triple H to get his chance against the WWE Champion by now. After all, The Game has gotten his way with many superstars during their main event pushes (Jinder Mahal, Dean Ambrose, among others). Hopefully, we'll see the legends square off down the road.
New Day vs. D-Generation X, anybody?
Christian and Triple H teamed up together a handful of times in WWE, but the two legends never once faced each other.
Triple H had his program with Edge, Christian's long-time friend and tag team partner. Yet, the latter never got his chance to take down the Cerebral Assassin, and vice versa. Unless Christian comes out of retirement for one more match, Triple H will never get to brag about defeating the former ECW and World Heavyweight Champion.
6 Sycho Sid
Sycho Sid had worked in WCW and WWE before eventually landing in the United States Wrestling Association. Sid returned to the WWF in 1995 and went up against a young, up-and-coming "Hunter Hearst Helmsley" in a pair of matches back in 1996.
Sid defeated Undertaker on the Aug. 19 during a Raw Championship Friday show. The two faced off on the Nov. 18 episode of Monday Night Raw, with Sid picking up the victory again. It wouldn't be long until Triple H eventually saw his main event push where he'd form DX with Shawn Michaels, Chyna, et al.
5 The Miz
Triple H has won some tag team matches against The Miz, and he did defeat the latter along with Chavo Guerrero in a handicap tag team match back in Dec. 2008. But that doesn't exactly count as a true victory against The Miz, since it wasn't one-on-one.
Big Show and The Miz defeated Triple H and Shawn Michaels (D-Generation X) on the Feb. 8, 2010 episode of Raw to become the new Unified Tag Team Champions. Miz and Big Show would win a rematch a month later.
The last time Miz and Triple H were involved in the same match? Back at the aforementioned Vengeance 2011 pay-per-view, where Awesome Truth took down Triple H and CM Punk. You get the feel that at some point, we will get to witness Triple H vs. The Miz. One-on-one. It's long overdue.
4 Rey Mysterio
The Master of the 619 first joined WWE in 2002, and he stayed there until 2015 before moving on to the independent circuit—and eventually Lucha Underground. Mysterio signed a two-year contract with WWE last year and is nearly halfway through the deal.
Mysterio has hinted at retirement, and time is running out on a match against Triple H. Even though he's spent approximately 15 years in WWE, Rey Mysterio has never had a match with The Game. The two legends have teamed up together at various points throughout their careers, and they squared off in a tag team match back in 2006.
May we finally see this match one day? If not, neither guy will be able to brag about defeating the other. Perhaps we'll see this match before Mysterio—undoubtedly a Hall of Famer—hangs up the boots on his wrestling career.
3 Seth Rollins
Triple H has been the subject of criticism due to his long list of superstars that he's buried rather than simply help put over. From Goldberg to Booker to Rob Van Dam, The Game really didn't do many favors for superstars when the chance was there for him to put them over.
Well, Seth Rollins is one of the few main event stars of the 21st century that Triple H wound up putting over rather than burying. The Shield defeated Evolution (Triple H, Randy Orton, and Batista) at the 2014 Extreme Rules and Payback pay-per-view. Rollins also defeated Triple H at WrestleMania in a singles match. That said, time is on the side of The Game to eventually take down The Architect.
2 Daniel Bryan
Daniel Bryan defeated Triple H in one of the first matches at WrestleMania XXX —hus earning his spot in the main event against Orton and Batista for the WWE World Heavyweight Championship. Bryan closed out the event with the match of his life, winning the title after forcing Batista to submit.
Triple H got a rematch against Bryan on the ensuing episode of Raw, which he lost. The latter had to deal with concussion and neck injuries and was retired from 2016 to '18, but he's going strong again and remains a world-class talent in the ring. You have to think that we'll see these two all-time greats in the ring again soon; Triple H has unfinished business with Bryan, and a rematch is truly inevitable. But, for now, Bryan leads the all-time series 2-0.
1 Roman Reigns
Give Triple H credit for doing his part in trying to help Roman Reigns get over. As mentioned in the Rollins entry, Triple H and Evolution lost a pair of matches to The Shield in 2014. Two years later, Triple H won the Royal Rumble event (the WWE World Heavyweight Championship was on the line in this one) to dethrone Reigns as champion.
Reigns and Triple H headlined WrestleMania 32 in Dallas, and The Big Dog closed out the event by defeating The Game via pinfall. Triple H took a hiatus from wrestling and hasn't crossed paths in the ring with Reigns ever since, but we're sure a rematch will happen at some point. Yet, for now, Reigns remains undefeated against this wrestling legend.