Wingo was born in Norcross, Georgia, in 1898. He attended Oglethorpe University in suburban Atlanta where he played as a catcher and a pitcher for the Oglethorpe Stormy Petrels baseball team during the 1917 and 1918 seasons. Wingo's older brother Ivey Wingo reached the major leagues in 1911 and became a fixture for the St. Louis Cardinals and Cincinnati Reds from 1911 to 1926.
Wingo was acquired by the Philadelphia Athletics late in the 1919 season and made his major league debut on September 9, 1919. He appeared in 15 games for the 1919 Athletics, compiling a.305 batting average in 59 at bats. Despite his strong batting average, Wingo returned to the minor leagues, playing for the Atlanta Crackers in 1920 and 1921 and for the Toronto Maple Leafs in 1922 and 1923. In 1922, he set a new International League record with 34 home runs. He followed up with a.352 batting average and 20 home runs in 1923.
Detroit Tigers
On August 20, 1923, the Toronto club sold Wingo to the Detroit Tigers for $50,000 with the caveat that he need not report to the Tigers until Toronto's season was over. In 1924, he appeared in 78 games for the Tigers, mostly as a pinch hitter but also in 30 games as a starter in the outfield. In 1925, Wingo took over from Heinie Manush as the Tigers' starting left fielder. He appeared in 130 games and had the best season of his career. He led that American League's left fielders with eight double plays turned and ranked among the league leaders with a.370 batting average,.456 on-base percentage, 104 runs scored and a 5.3 wins above replacement rating for position players. All three Detroit outfielders in 1925 ranked among the league's batting leaders -- Wingo with a.370 average, Harry Heilmann winning the batting title with a.393 average and Ty Cobb with a.378 average. This was the only time in MLB history that every member of an outfield hit.370 or better. At the end of the 1925 season, Wingo finished twelfth in the American LeagueMost Valuable Player voting. In 1926, Wingo appeared in 108 games for the Tigers, but lost his job as the team's regular left fielder, starting 57 games in left field and 11 in right field, as his batting average dropped by 88 points to.282. His playing time declined to 75 games in 1927 as his batting average dropped further to.234. In his final year in the major leagues, he appeared in 87 games for the 1928 Tigers and compiled a.285 batting average. In six major league seasons, Wingo appeared in 493 games, scored 224 runs, collected 409 hits, 191 RBIs, and 211 bases on balls. Boosted by his 1925 season, Wingo had a career.308 batting average, with a.404 on-base percentage and a.423 slugging percentage.
Minor leagues
After the 1928 season, Wingo was acquired on waivers by the San Francisco Seals of the Pacific Coast League. The deal was combined with the Tigers' January 1929 purchase of Roy Johnson with Wingo being given a value of $7,500 for purposes of the transaction. Wingo played in the outfield for the Seals and compiled batting averages of.350 in 1929,.348 in 1930, and.314 in 1931. In May 1931, he became the first player to hit a home run out of the Seals' new ballpark. He continued to play for the Chattanooga Lookouts in 1931 and the Scranton Miners and Toronto Maple Leafs in 1932.
Later years
In January 1934, Wingo returned to Detroit and played for the Tivoli club in the Detroit Baseball Federation. After retiring from baseball, he remained in Detroit and worked as a driver and safety inspector for Ford Motor Company. In October 1964, Wingo was involved in an traffic accident in Allen Park, Michigan, in which his truck was struck from behind by a driver who had been drinking. Wingo was thrown from the cab of his truck and dragged under the truck until it hit a fence. He was taken to Outer Park Hospital in Lincoln Park, Michigan, where he died at age 66.
