As a team captain in hoops, he was a three-time All-SEK 1st-team choice and earned All-State honors 3 consecutive years while guiding Parsons to the state tournament as a sophomore and senior.

He played all five positions at times for the small school program, and set career marks for assists, steals, blocks, and 3-point field goals.

In track & field, he ran sprints (100m, 200m, 4 × 100 m, 4 × 400 m) as a junior and senior and even qualified for the state championships in three events during his final year.

While serving primarily as a backup as a junior, he led the Maryland Terrapins to their first Atlantic Coast Conference title since 1985 as a senior in 2001.

He took his first career snaps for the Vikings on the final two plays of the 2005 NFL season, taking a knee both times.

[3] In order to get more experience, Hill spent the spring of 2003 with the Amsterdam Admirals of NFL Europe, where he led the league in passing yards and tied for second in touchdowns.

Hill entered the 2006 NFL preseason third on the San Francisco 49ers depth chart, behind Trent Dilfer and Alex Smith.

Hill completed 13 of 20 passes for 148 yards with one interception in the San Francisco 49ers' 17-13 preseason opening loss to the Denver Broncos on August 16, 2007.

"[4] Since Dilfer's injury was serious enough to sideline him for the rest of the season, Hill made his first NFL start on December 15, 2007, in a victory against the Cincinnati Bengals.

Hill suffered a back injury during the week 16 game against the Tampa Bay Buccaneers, when rookie Gaines Adams hit him after a throw, drawing a 15-yard personal foul.

The undrafted Hill competed for the starting job against Alex Smith and J. T. O'Sullivan in training camp and the 2008 preseason.

O'Sullivan ended up getting the job and Hill became the primary backup after Smith was put on injured reserve early in the season.

Shortly after the Seahawks game,[9] reports surfaced that Nolan and offensive coordinator Mike Martz allegedly made up stories about Hill having a tired arm in the preseason so that O'Sullivan, who played for Martz when he was offensive coordinator of the Detroit Lions, would win the starting job without a real challenge.

On Monday Night Football against the heavily favored Arizona Cardinals, Hill delivered a solid performance in the first half.

However, in the second half, Hill threw an interception at a critically bad time to give the Cardinals the 24–29 lead.

Coincidentally, on Monday Night Football of the 2007 season against the Cardinals, the 49ers drove to the goal line in a similar fashion, and were able to get the game-winning touchdown.

Hill convinced his coach to leave him in the game and then led the 49ers on an 80-yard drive, finishing with a touchdown pass to Isaac Bruce for his 1000th career reception.

Now down 16-10 and under three minutes left on the clock, Hill got the ball back and completed a 48-yard touchdown pass to Josh Morgan.

The 49ers defense intercepted Marc Bulger ending any chance of a Rams comeback and capping Hill's first big late-game rally win.

In a week 17 thriller against the Washington Redskins, Hill was showing difficulty, throwing an interception in the first half and no touchdowns.

Hill was named the starter for the 49ers preseason opener versus the Denver Broncos, where he would throw only two passes, completing both.

Hill led the 49ers to a lead near the end of the game, but Brett Favre ultimately threw a 30-yard touchdown pass with two seconds left to win for the Vikings.

[17] Hill finished the 2014 season with 1,657 passing yards, 8 touchdowns, 7 interceptions, and an 83.9 quarterback rating in 9 games with 8 starts.