2014: five-year-old season

The Pizza Man started his five-year-old campaign on June 21, 2014 at Arlington in the Black Tie Affair Handicap. He raced in third place through the early portion of the race then closed ground to win by half a length.^[2] On July 12, he finally won his first graded stakes race, the 1+1⁄2-mile Stars and Stripes, in front-running fashion. "I had the best horse in the race, so I took the lead and went with it," said Geroux. "The plan was to get to wherever he was comfortable and he was comfortable on the lead."^[13]

The win gave The Pizza Man an automatic entry in the $400,000 American St. Leger in August.^[13] For the 1+11⁄16-mile marathon, he faced a strong field of horses from across not only North America but Europe as well, including the previous year's winner Dandino (GB) and the favorite, Eye of the Storm (IRE). The Pizza Man and Eye of the Storm raced just behind the early pace, then made their move entering the final turn. The Pizza Man drew away from Eye of the Storm then withstood a late run from Dandino to win by a length. "I had the perfect race," said Dandino's jockey Frankie Dettori. "Turning in I thought we would win, but (The Pizza Man) never stopped. He ran really hard to the line. He's coming back to form now."^[12]

The Pizza Man then shipped to Woodbine racetrack in Toronto to take on Grade I company for the first time in the Northern Dancer Turf Stakes. He stalked the pace, then started to make a run in the stretch but "evened out" and was passed by several late closers, finishing fifth.^[14] He then started in the Canadian International, also at Woodbine, held on October 19. He raced just off the pace and took the lead entering the stretch. He was passed by other horses in mid-stretch but continued to chase, finishing fourth.^[15] His final start of the year was in the Hollywood Turf Cup at Del Mar in late November, where he finished third.^[2]

2015: six-year-old season

The Pizza Man was given a long layoff, spending much of the winter at his owner's Illinois farm. "I think we had a tired horse at the end of the year," said Papiese.^[16] The horse made his 2015 debut on May 30 in the Opening Verse Stakes at Churchill Downs, winning the 1+1⁄16-mile race by 2+1⁄2 lengths.^[17] On July 11, he returned to Arlington to defend his title in the Stars and Stripes as the 4–5 favorite. He raced behind a slow pace set by Roman Approval then made his move and hit the lead in mid-stretch. Roman Approval fought back and the two dueled to the wire, with The Pizza Man prevailing by a neck.^[18]

For his next start in August, Papiese chose to enter the gelding in the Grade I Arlington Million rather than attempt to defend his title in the American St. Leger. Papiese felt confident despite the world-class field in the Million. "He has never been better," he said. "I respect all of the people here — all the great owners and trainers and jockeys — and all of the horses we're running against, but I wouldn't trade places with anybody."^[8] On a soft turf course, The Pizza Man struggled in the early going but made a strong move down the stretch to win by a neck over Big Blue Kitten. "When I put him outside he started to hold up and grabbed the bit again," said Geroux. "I was thinking 'Oh boy, he's going for a big one here!' He is a local horse and even going to the track there was a lot of people cheering for us, and I'd like to thank them."^[19] The Pizza Man became the first Illinois-bred to win the Arlington Million.^[20]

On October 3, The Pizza Man was entered in the Shadwell Turf Mile at Keeneland. Racing at the back of the field in the early going, he closed "like a freight train" down the stretch and fell just short, finishing a head behind Grand Arch.^[21] "He couldn’t keep up early, so I let him settle," said Geroux. "When I asked him to run, it took him a little bit longer than usual because the race is shorter, but the last quarter of a mile he was flying."^[22]

The Pizza Man was next entered in the Breeders' Cup Turf on October 31, where he faced an outstanding field headed by Golden Horn, winner of the Derby and Prix de l'Arc de Triomphe, and Found, a three-year-old filly who had run second in the Irish Champion and Champion Stakes. The Pizza Man was no match for these two but finished a creditable fifth.^[23] "No excuse," said Geroux. "We were right behind Golden Horn all the way. I had the filly stuck on my inside. Turning for home he made a little run, but just got tired."^[24]

Papiese had planned to send the Pizza Man overseas to contest the Japan Cup but the gelding came down with a lung infection and would not have been able to recover in time.^[25] Instead, he traveled to Del Mar, California for the Hollywood Turf Cup on November 26. Ridden by new jockey Mike Smith, he won by two lengths as the heavy favorite. "Mike let him run his race, and when he gets to run his race, he's tough to beat," said Papiese. "Mike said he was going to be eight to 10 lengths off of it, and I said, 'You're going to love the afterburners when they kick in.'"^[26]

The Pizza Man finished the year with four wins and a second from six starts. The Illinois Thoroughbred Breeders and Owners Foundation honored him as the 2015 Illinois-bred Champion Turf Male, Champion Handicap Male, and Illinois Horse of the Year.^[27] He finished third in the Eclipse Award balloting for North American Champion Turf Male with 41 votes, behind Great Britain's Golden Horn and winner Big Blue Kitten.^[28][29]

2016: seven-year-old season

The Pizza Man started his seven-year-old campaign with a fifth place finish in the Gulfstream Park Handicap on February 6, 2016. "He really didn't like the Gulfstream turf at all,” said Brueggemann. "That was the first time I had him on something that he didn't like. We're hoping he can still compete as a year older but I know how I feel when I'm a year older."^[30] He then suffered three more losses in a row, placing fourth in the Wise Dan in June, fourth in the Stars and Stripes in July, and sixth in the Arlington Million.^[2]

On September 18, The Pizza Man traveled to Woodbine for his second appearance in the Northern Dancer Turf Stakes. With new jockey Flavien Prat, he raced in second on the outside of pacesetter World Approval, then fought his way to the lead. He then withstood a late rush by Wake Forest to win by a head, with World Approval a further head back in third. The win sent The Pizza Man's earnings over $2 million, and made him the first Illinois-bred horse to win the race. Papiese complimented Prat for adapting his tactics to the slow pace set by World Approval. "The game plan was to save ground and let him run in the stretch, but you go to 'Plan B' when 'Plan A' is pretty much out the window," he said.^[31]

The Pizza Man next entered the Canadian International at Woodbine on October 16, finishing fourth behind Irish-bred Erupt.^[32] He finished the year with a third-place finish in the River City Handicap.^[2]

2017: eight-year-old season

The Pizza Man was given a long layoff, then returned on June 17, 2017 in the Black Tie Affair Handicap, finishing fourth. He next entered the Stars and Stripes Stakes for the fifth time, where he was made the favorite despite growing concerns that he had lost a step.^[33] The Pizza Man rated close behind a slow early pace then made his move in the final turn, hitting the lead in mid-stretch. Near the finish line though he was caught by Keystoneforvictory, who went on to win by 1+1⁄2 lengths. "He felt good", said Geroux. "Turning for home I thought I was going to get the win, but the one horse just ran him down the last eighth of a mile. He ran great, I think he's improved on his last race and I think he's moving in the right direction. He's a little bit older now and it might take him a bit longer to get to his top form."^[34]