Dick Littlefield was born in Detroit on March 18, 1926. He went to Cooley High School, leaving after 11 grades. By 1941, he was playing amateur baseball in Detroit and he also was a good amateur hockey player.

His professional career began only after his service in the United States Navy (March 1944 to May 1946) was done.  He was signed after 4 or 5 weeks out, by the Red Sox and was sent to Oneonta in the Canadian American League.

He was dropped down to Class D in 1947, and pitching for Wellsville in the Pennsylvania-Ohio-New York League. In 1948 he was assigned to the Roanoke Red Sox in the Class-B Piedmont League and jumped to the Single-A Scranton Miners (Eastern League) in 1949. In September 1949, he was signed to a Boston Red Sox contract and invited to join the team for spring training.

He spent the first half of 1950 with the Birmingham Barons before being called to Boston and given a start in July. The 1950 Red Sox set a franchise record for runs scored, but cycled through a number of pitchers.  Dick received his big-league baptism in front of 58,375 at Yankee Stadium. Two pitches did him in. He walked leadoff man Phil Rizzuto, on four pitches and the next man up, Gene Woodling, tagged him for a home run. He then settled down until tiring in the sixth. A walk, again followed by a home run to right field by Cliff Mapes, gave the Yankees the win.  In all, he appeared in 15 games, winning two of them, with an ERA of 9.26. In December he was traded to the White Sox.

He lasted a full season, but not a full year with the White Sox. After May, he spent the rest of the season pitching for their Memphis farm club. In November 1951, he was part of an eight-player swap with the St. Louis Browns, but before he played for the Browns, he pitched 28 games for his hometown Detroit Tigers.  And then he was on his way back to the Browns via waivers in August.

In 1953 he spent the full season with the Browns and after the season, pitched for Cienfuegos in Cuban winter league ball. Like the rest of the Browns, he traded in his uniform for a Baltimore Orioles once the franchise moved east. He wasnt with the Os long, however, before he switched teams to the Pittsburgh Pirates in May.

With the 54 Pirates, he won a career-high 10 games, and recorded a very good 3.60 ERA. He started the 1956 season with the Pirates, but was traded to the St. Louis Cardinals in May. In June, he was traded again, part of a nine-player deal with the New York Giants.

In December 1956, he was traded to the Brooklyn Dodgers for Jackie Robinson. But Robinson had no desire to join the Giants and elected to retire instead, so the trade was therefore voided. So Dick was back with the Giants until mid-April, when he was traded to the Chicago Cubs, his ninth team, and in only nine years.

In 1957, he appeared in 48 games, all but two in relief and was dealt again, in March 1958, purchased by the Milwaukee Braves. Given that hed gone from a team in the cellar, to 1957s World Champion Braves, he was full of optimism. But the Braves really didnt feel they needed him and he appeared in only four games, spending most of the year in Wichita. But he was not brought back up and his time in the major leagues was over.

In 1959 he pitched for Louisville, and in 1960 he pitched for Louisville and Indianapolis. In 1961 he both pitched and coached for the Dallas-Fort Worth Rangers and in 1962 he managed the team before hanging them up. 

After baseball, Dick Littlefield worked in a tool and die factory, and died on November 20, 1997, at age 71, in Detroit.