Duke Dawson would never play a snap before being released after one season while Whitehead and Carlton Davis would both start in Super Bowl LV.

[14] Throughout training camp, Whitehead competed for a role as a starting safety against Keith Tandy, Chris Conte, and Justin Evans.

[15] Head coach Dirk Koetter named Chris Conte and Justin Evans the starting safeties to begin the season, with Whitehead listed as a backup behind Keith Tandy and Isaiah Johnson.

[16] On September 9, 2018, Whitehead made his professional regular season debut in the Buccaneers' season-opening 48–40 victory at the New Orleans Saints, appearing almost entirely on special teams.

[17] On October 14, 2018, Whitehead earned his first career start after Chris Conte was placed on injured reserve due to a knee injury.

The following week, Whitehead made one solo tackle and a pass deflection before sustaining a hamstring injury and exiting during the second quarter of a 38–17 win against the Detroit Lions.

[23] He finished his sophomore season in 2019 with a total of 69 combined tackles (50 solo), nine pass deflections, one interception, and one fumble recovery in 14 games and 14 starts.

[24] Defensive coordinator Todd Bowles elected to retain Whitehead as the starting strong safety and paired him with rookie Antoine Winfield Jr. to kick off the regular season.

In Week 3 at the Denver Broncos, Whitehead recorded five combined tackles (four solo) and had his first career sack on quarterback Jeff Driskel during a 28–10 victory.

On January 9, 2021, Whitehead started in his first playoff appearance and only had one pass deflection during a 31–23 win over the Washington Football Team in the NFC Wildcard Game.

On January 24, 2021, Whitehead started in the NFC Championship Game and recorded five combined tackles (four solo) and two forced fumbles, with one being on running back Aaron Jones that was recovered by teammate Devin White during the Buccaneers' 31–26 victory at the Green Bay Packers.

[28] On January 7, 2021, Whitehead started in Super Bowl LV, but was limited to two solo tackles as the Tampa Bay Buccaneers routed the Kansas City Chiefs 31–9.