Evans played the second-most career games for the Red Sox of any player, surpassed only by Carl Yastrzemski.

Dwight attended Granada Hills High School in the tenth grade, but was not happy with the poor treatment he received from the baseball coaches.

Early in his major league career, Evans was primarily a defensive standout (he would eventually receive eight Gold Glove Awards) with a modest bat.

In the historic sixth game, with the score tied 6–6 in the 11th inning, he made a spectacular catch of a drive hit by Reds second baseman Joe Morgan, then threw to first base to complete an inning-ending double play.

On Opening Day of 1982, the Red Sox were visiting the Milwaukee Brewers, where Evans watched Sixto Lezcano's famous walk off grand slam in the bottom of the Ninth sail over his head.

Brewers announcer Bob Uecker called the homerun as follows: "Here's a drive to deep right-center, way back goes Evans.

The Red Sox went on to win the AL East, and defeated the California Angels in seven games in the 1986 ALCS; Evans batted 6-for-28 (.214) with a home run and four RBIs.

Boston then lost the 1986 World Series to the New York Mets in seven games; Evans batted 8-for-26 (.308) with two home runs and nine RBIs.

As recently as 2016, Evans has said publicly that he has never watched any highlight films of that World Series because the memory remains too painful for him to bear.

He was named an All-Star for the third time of his career, won his second Silver Slugger Award, and finished fourth in MVP voting.

Based on his uncertain medical status, Evans was released by the Orioles in spring training on March 15, 1992.

Evans spent two seasons as an MLB hitting coach; 1994 with the Colorado Rockies, and 2002 with the Red Sox.

[15] Evans was dropped from the Baseball Hall of Fame ballot when he did not receive the minimum five percent of votes in his third year of eligibility.

Evans' low vote total in 1999 is attributed to the appearance of future Hall of Fame players Nolan Ryan, George Brett, Robin Yount, and Carlton Fisk on the 1999 ballot.

Based on his win shares metric, baseball statistician Bill James has argued that Evans is a worthy candidate for induction.

[19] In January 2021, Evans was ranked 10th by Joe Posnanski of The Athletic in a listing of the 100 greatest eligible players not in the Hall of Fame.