In what could be the last starts with their respective clubs, De La Rosa will try to help the Rockies stop their longest road skid in nearly two years when he opposes Jackson and the Cubs on Tuesday night.
De La Rosa (11-6, 4.19 ERA), a free agent next season, has been rumored to be one of the top pitchers on the trade market with Thursday's deadline approaching, though more recent reports have the Rockies leaning toward keeping him.
NL-worst Colorado (43-62) can assure itself of draft pick compensation if the left-hander were to sign elsewhere by holding on to him and making a $14 million qualifying offer for next season.
''If I get traded, I get traded,'' De La Rosa said. ''I don't have to think about those things right now.''
De La Rosa has no doubt opened some eyes with the way he's pitched recently. Since allowing a season-worst eight runs in a road loss to the Los Angeles Dodgers on June 18, he's gone 5-0 with a 3.05 ERA in his last six outings.
The left-hander also has allowed one earned run or less while going at least six innings in three straight starts.
De La Rosa is 3-0 with a 2.37 mark in five career starts against the Cubs (43-61), holding them to one earned run with nine strikeouts over seven innings in a 4-3 win in his only start at Wrigley Field in April 2011.
All-Star Anthony Rizzo is hitless in four career at-bats versus De La Rosa, but he's batting .297 with eight home runs in 101 at-bats against left-handers this season. He went 1 for 4 with two RBIs in Monday's 4-1 win in the opener of this four-game set.
Now the NL Central-worst Cubs will try to pick up consecutive victories for only the second time since July 5.
After sending top pitchers Jeff Samardzija and Jason Hammel to Oakland earlier this month, Chicago shipped former Gold Glove second baseman Darwin Barney to the Dodgers for a player to be named Monday.
The Cubs reportedly have been trying to move Jackson (5-11, 5.76) and what's left of his four-year, $52 million contract, but he hasn't helped his stock by going 0-4 with a 7.47 ERA in six starts since his last win June 20.
"At the present time, I'm right here with Chicago and that's what I'm focusing on and not looking too far down the road," Jackson told MLB's official website.
The right-hander will try to recover from another poor outing after giving up five runs over five innings in Thursday's 13-3 home loss to San Diego. He's 0-3 with an 11.57 ERA in his last four at home and 1-3 with a 12.66 ERA in eight versus Colorado.
Carlos Gonzalez might be able to get on track since he's 7 for 9 with six RBIs lifetime against Jackson. The two-time All-Star went 0 for 4 with two strikeouts Monday following a two-game absence because of an ankle injury and is batting .152 in his last 20 games.
The Rockies have totaled 15 runs during a seven-game road losing streak after finishing with six hits in the opener. They haven't dropped eight straight on the road since a nine-game skid in September 2012.
Colorado continues to play without injured NL batting leader Troy Tulowitzki, but Justin Morneau is hoping to rejoin the club after missing 10 games with a strained neck.